Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008

Size: px
Start display at page:

Download "Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008"

Transcription

1 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008

2 p-phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron-Transfer Properties Mateusz Wielopolski, [a] Carmen Atienza, [a,b] Timothy Clark, [c] Dirk M. Guldi, [a] * Nazario Martín [b,d] * [a] Department of Chemistry and Pharmacy Interdisciplinary & Center for Molecular Materials (ICMM) Friedrich-Alexander-Universität Erlangen-Nürnberg Fax: (+49) dirk.guldi@chemie.uni-erlangen.de [b] Departamento de Química Orgánica Facultad de Ciencias Químicas Universidad Complutense de Madrid Ciudad Universitaria s/n Madrid (Spain) nazmar@quim.ucm.es [c] Interdisciplinary Center for Molecular Materials Friedrich-Alexander-Universität Erlangen-Nürnberg Computer-Chemie-Centrum Naegelsbachstrasse , Erlangenand, Germany [d] Instituto Madrileño de Estudios Avanzados en Nanociencia (IMDEA. Nanociencia) 1

3 Experimental Section Molecular Modelling: Calculations were performed using the program packages Gaussian03 [35] and VAMP 10.0.[36] Molecular properties in the electronic ground state were computed using density functional theory at the B3LYP/6-31G* (/6-311G**) and the B3PW91/6-31G* (/6-311G**) levels and the restricted Hartree-Fock formalism with the semi-empirical AM1* Hamiltonian.[S1] Excited-state calculations used a singles-only configuration interaction (CIS) expansion with an active window of the three to six highest occupied and lowest unoccupied molecular orbitals and the AM1 Hamiltonian.[S2] Test calculations with a singles only CI with up to 30 active orbitals suggested that this level of theory is adequate for the problem. Excited-state geometries were optimized in vacuo using numerical CI gradients.[s3] Solvent effects were simulated in single-point calculations on the gas-phase optimized geometries using the self-consistent reaction field solvation models with solvent-excluded surfaces with atomic radii equal to 120% of those given by Bondi.[S4] Local electron affinity and local ionization energy calculations [S5] on the AM1* optimized structures were performed using Parasurf 07 A1 [S7] and visualized with Tramp 1.1d.[S7] Compound 7: Compound 4 (1.14 g, 2.37 mmol) and p-ethynylbenzaldehyde 6 (324 mg, 2.48 mmol) were dissolved in dry piperidine (25 ml) and the system was flushed with argon. Bis(triphenylphosphine)-palladium dichloride ( mg, mmol), triphenylphosphine (30.95 mg, mmol) and copper(i) iodine (22.56 mg, mmol) was added. The mixture was stirred at room temperature for 16h. Dichloromethane was added to the residue and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed in vacuo. The crude product was purified by flash chromatography on silica gel using hexane:acoet (9:1) as eluent to afford 7 (1.45 g, 2.61 mmol) as yellow solid. Yield 41%. Mp ºC. 1 H- NMR (200 MHz, CDCl 3, 25ºC): δ= (s, 1H), 7.84 (d, J = 8.54 Hz, 2H), 7.64 (d, J = 8.05 Hz, 2H), 7.10 (s, 1), 7.00 (s, 1H), 4.00 (q, J = 1.95 Hz, 4H), (m, 4H), (m, 4H), (m, 8H), ppm (m, 6H). 13 C- NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , 93.06, 89.68, 70.14, 69.78, 31.54, 2

4 31.49, 29.21, 29.14, 25.70, 25.64, 22.61, 22.57, ppm. FTIR (KBr): ν= 669, 756, 844, 1215, 1276, 1384, 1467, 1494, 1600, 1701, 2208, 2858, 2871, 2931, 2956, 3018, 3419 cm -1. MS (ESI): m/z (%): 486 (40) [M+], 402 (12), 316 (100). Anal. Calcd for C 27 H 33 BrO 3 : %C: 66,80, %H: Found: %C: 66,75, %H: Bromo-5-trimethylsilylacethynyl-1,4,bishexyloxybenzene 8 : 2-bromo-5-yodo-1,4- dihexiloxibenzene 4 (1.23 g, 2.55 mmol) was dissolved in dry piperidine (25 ml) Pd(PPh 3 ) 2 Cl 2 (44.22 mg, mmol), PPh 3 (33.31 mg, 0.12 mmol) and CuI (24 mg, 0.12 mmol) were added and stirred for 5 min, then trimethylsilylacetylene (4 ml, 2.81 mmol) was added to the solution. The mixture was stirred at room temperature for 3 h. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane:acoet (9:1). The product was obtained as a white solid 8 (1.01 g, 2.22 mmol). Yield 87%. M.p.: ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 7.05 (s, 1H), 6.95 (s, 1H), (m, 4H), (m, 4H), (m, 4H), (m, 4H), (m, 6H), 0.26 (s, 9H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , 99.55, 70.40, 70.04, 32.01, 31.92, 30.13, 29.65, 29.54, 26.08, 26.05,23.05, 23.00, 14.49, ppm. DEPT 135 (75 MHz, CDCl 3, 25ºC): δ= (CH), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ),23.05 (CH 2 ), (CH 2 ), (CH 2 ), ppm (CH 3 ). FTIR (KBr), ν: 829, 856, 991, 1035, 1056, 1213, 1269, 1467, 1488, 1500, 2920, 2941, 2954 cm -1. EM m/z (EI), (%I): 454 (M+, 40), 368 (20), 286 (42), 271 (65), 43 (100). Compound 9: Compound 8 (1.79 g, 3.94 mmol) and 6 (539 mg, 4.14 mmol) were dissolved in dry toluene (30 ml) and the system was flushed with argon. Tetrakis(triphenylphosphine)-palladium (228 mg, mmol) and copper (I) iodine (37.57 mg, mmol) were added. The mixture was refluxed for 17 h. Ethyl acetate was added to the residue and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel hexane: CH 2 Cl 2 (20:1) as eluent to afford 9 (510 mg, mmol) as a yellow solid. Yield 65%. Mp ºC. 1 H- NMR (300 MHz, CDCl 3, 25 ºC): δ= (s, 1H), 7.86 (dd, J 1 = 6.59 Hz, J 2 =

5 Hz, 2H), 7.67 (brs, 2H), 3.99 (t, J = 6.1 Hz, 4H), (m, 4H), (m, 4H), (m, 8H), (m, 6H), 0.27 ppm (s, 9H). 13 C- RMN (75 MHz, CDCl 3 ): δ= ,154.52, , , , , , , , , , , 94.25, 90.55, 69.92, 32.01, 31.97, 29.69, 29.65, 26.13, 23.04, 14.48, 14.42, 0.33 ppm. FTIR (KBr): ν= 669, 756, 1215, 1465, 1488, 1600, 1701, 2399, 2931, 2958, 3018 cm -1. MS (ESI): m/z (%): 500 (100) [M + ], 319 (84), 73 (24), 43 (47). Anal. Calcd for C 32 H 42 O 3 Si: %C: 76.45, %H: Found: %C: 76.56, %H: Triisopropylsilylethynyl-5-trimethylsilylethynyl-1,4-bishexyloxybenzene 11 : Compound 8 (1.38 g, 3.04 mmol) was dissolved in dry toluene (25 ml), the system was flushed with argon. Pd(PPh 3 ) 4 ( mg, mmol), CuI (29 mg, mmol) and diisisopropylamine (2mL) were added. The mixture was stirred for 5 min and then triisopropylsilylacetylene (0.4 ml, 2.81 mmol) was added. The mixture was refluxed for 24 h. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane:acoet (9:1). The product was obtained as a white solid 11 (1.45 g, 2.61 mmol). Yield 86%. M.p.: ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 6.88 (s, 2H), (m, 4H), (m, 4H), 1.57 (br, 3H), (m, 4H), (m, 8H), 1.14 (br, 18H), (m, 6H), 0.25 ppm (s, 9H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , 99.57, 70.40, 70.04, 32.01, 31.92, 29.65, 29.53, 26.08, 26.05, 23.05, 23.01, 19.11, 14.50, 14.45, 11.76, 0.37 ppm. DEPT 135 (75 MHz, CDCl 3 ): δ= (CH), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 3 ), (CH), (CH), (CH), 0.37 ppm (CH 3 ). FTIR (KBr): ν= 557, 613, 661, 810, 840, 862, 999, 031, 1058, 1201, 1222, 1247, 1272, 1384, 1404, 1467, 1498, 2150, 2866, 2895, 2941 cm -1. EM m/z (EI), (%I): 554 (M, 100), 427 (20), 343 (20), 73 (32), 43 (84). 2-Triisopropylsilylethynyl-5-ethynyl-1,4-bishexyloxybenzene 12 : Compound 11 (258 mg, mmol) was dissolved in a mixture of THF:MeOH (1:1) 40 ml and K 2 CO 3 ( mg, mmol) was added to the solution. The solution was stirred at room temperature for 2h. The mixture was extracted with dichloromethane and washed with water (2 x 50mL). The organic phase was dried with MgSO 4 and the solvent was 4

6 removed under vacuum. The product was purified by flash chromatography on silica gel using hexane:ch 2 Cl 2 (10:1) as eluent. The product was obtained as a yellow solid 12 ( mg, 0.95 mmol). Yield 100%. M.p: ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 6.92 (brs, 2H), 3.94 (t, J = 6.5 Hz, 2H), 3.93 (t, J = 6.4 Hz, 2H), 3.33 (s, 1H), (m, 4H), (m, 4H), (m, 8H), 1.26 (s, 21H), ppm (m, 6H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , 81.98, 79.92, 70.50, 70.21, 31.89, 29.51, 29.45, 26.03, 25.95, 22.97, 19.09, 14.41, ppm. DEPT 135 (75 MHz, CDCl 3 ): δ= (CH), (CH), (CH), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 3 ), 14.41(CH 3 ), ppm (CH 3 ). FTIR (KBr): ν= 659, 713, 729, 769, 810, 999, 1031, 1056, 1199, 1220, 1272, 1467, 1498, 1541, 2152, 2864, 2895, 2923, 2943, 3421 cm -1. EM m/z (EI), (%I): 482 (M, 7), 382 (20), 298 (12), 214 (100), 55 (19). Compound 13: Compound 5 (97.89 g, mmol) and compound 12 ( mg, mmol) were dissolved in dry THF (25 ml) and the system was flushed with argon. Tetrakis(triphenylphosphine)-palladium (24.26 mg, 0.02 mmol), copper (I) iodine (4 mg, 0.02 mmol) and diisopropylamine ( 1mL) were added. The mixture was refluxed for 24h. Ethyl acetate was added to the residue and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane:ch 2 Cl 2 (20:1) as eluent to afford 13 ( mg, 0.28 mmol) as a yellow solid. Yield 67%. 1 H-NMR (300 MHz, CDCl 3, 25º): δ= (s, 1H), 7.84 (dd, J 1 = 6.59 Hz, J 2 = 1.65 Hz, 2H), 7.58 (dd, J 1 = 6.59 Hz, J 2 = 1.65 Hz, 2H), 6.95 (brs, 2H), 4.01 (t, J = 6.2 Hz, 4H), (m, 4H), (m, 4H), (m, 8H), 1.00 (brs, 3H), 0.8 (s, 18H), ppm (m, 6H). 13 C-NMR (75 MHz, CDCl 3, 25 ºC): δ= , , , , , , 125.0, , , , ,107.23, 86.12, 88.0, 68.46, 31.54, 29.53, 25.65, 22.5, 18.67, 13.97, ppm. FTIR (KBr): ν= 669, 756, 1215, 1465, 1488, 1600, 1701, 2399, 2931, 2958, 3018 cm -1. MS (ESI): m/z (%): 585 (100) [M + ], 444 (80), 73 (45), 43 (60). Anal. Calcd for C 38 H 54 O 3 Si: %C 77.76, %H Found: %C: 77.56, %H: Compound 14: Compound 9 (884.2 mg, 1.75 mmol) was dissolved in a mixture of THF:MeOH (1:1) 40 ml and K 2 CO 3 ( mg, 1.75 mmol) was added to the 5

7 solution. The solution was stirred at room temperature for 12h. The mixture was extracted with dichloromethane and washed with water. The organic phase was dried with MgSO 4. The solvent was removed and the product was purified by flash chromatography on silica gel using hexane:acoet (15:1) as eluent. The product was obtained as a yellow solid 14 (686 mg, 1.42 mmol). Yield 81 %. Mp ºC. 1 H- NMR (300 MHz, CDCl 3, 25ºC): δ= 9.95 (s, 1H), 7.81 (dd, J 1 = 6.61 Hz, J 2 = 1.79 Hz, 2H), (d, 2H), 6.93 (brs, 2H), (m, 4H), (m, 4H), (m, 12H), ppm (m, 3H). 13 C-NMR (75 MHz, CDCl 3, 25 ºC): δ= , , , , , , , , , , , 94.30, 90.31, 80.23, 70.05, 69.92, 31.98, 31.93, 30.12, 29.64, 29.50, 26.14, 26.0, 23.05, 23.0, ppm. MS (ESI): m/z (%): 430 (M, 80), 429 (M +, 70), 230 (55), 206 (45). Anal. Calcld for C 29 H 34 O 3 : %C 80.89, %H Found: %C: 80.56, %H: Compound 15: Compound 14 ( mg, mmol) and compound 4 (140 mg, mmol) were dissolved in dry piperidine (15 ml) and the system was flushed with argon. Bis(triphenylphosphine)-palladium dichloride (6 mg, 8.12x10-3 mmol), triphenylphosphine (4.26 mg, 0.016mmol) and copper(i) iodine (3 mg, mmol) were added. The mixture was stirred at room temperature for 3h. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane: CH 2 Cl 2 (20:1) as eluent. The product was obtained as a yellow solid 15 (210 mg, mmol). Yield 14%. M.p.: ºC. 1 H- NMR (200 MHz, CDCl 3, 25ºC): δ= (s, 1H), 7.87 (d, J = 8.3 Hz, 2H), 7.66 (d, J = 7.92 Hz, 2H), 7.09 (brs, 1H),7.00 (brs, 2H), 6.98 (s, 1H), (m, 8H), (m, 8H), (m, 8H), (m, 16H), ppm (m,12h). 13 C- NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , 77.23, 76.73, 76.28, 74.94, 73.91, 73.12, 69.94, 69,83, 69.75, 69.54, 31.54, 31.51, 29.67, 29.18, 29.14, 29.09, 25.63, 25.59, 22.60, 22.57, 18.67, 18.64, 17.76, 16.22, 16.02, 15.74, ppm. FTIR (KBr): ν= 650, 745, 770, 800, 1126, 1310, 1645, 2255 cm -1. EM m/z (ESI), (%I): 783 (M +, 70),705 (55), 604(45), 579 (35). 6

8 Compound 16: Compound 8 (70.22 mg, mmol) and compound 14 (70 mg, mmol) were dissolved in dry THF (15 ml) and the system was flushed with argon. Tetrakistriphenylphosphine palladium (8.89 mg, 7.7x10-3 mmol), copper(i) iodine (1.46 mg, 7.7x10-3 mmol) and diisopropylamine (1mL) were added. The mixture was heated for 28 h. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane: AcOEt (9:1) as eluent. The product was obtained as a yellow solid 16 (20 mg, mmol). Yield 17%. M.p: ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= (s, 1H), 7.88 (d, J = 8.23 Hz, 2H), 7.67 (d, J = 8.24 Hz, 2H), 7.02 (brs, 2H), 6.97 (br, 2H), 4.05 (t, J = 6.5 Hz, 8H), (m, 8H), (m, 8H), (m, 16H), (m, 12H), 0.27 ppm (s, 9H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , , 94.31, 92.29, 91.69, 90.71, 70.11, 70.0, 69.87, 69.82, 32.01, 29.69, 29.65, 26.16, 26.12, 26.97, 23.05, 14.45, 0.36 ppm. DEPT 135 (75 MHz, CDCl 3, 25ºC) : δ= (CHO), (CH), (CH), (CH), (CH), (CH), (CH), (CH 2 ), 70.0 (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), (CH 2 ), 0.36 ppm (CH 3 ). FTIR (KBr): ν= 669, 756, 1215, 1465, 1488, 1600, 1701, 2399, 2931, 2958, 3018 cm -1. EM m/z (ESI), (%I): 802 (M +, 70), 619 (80), 413 (30). Compound 17: 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= (s, 2H), 7.87 (d, J = 8.5 Hz, 4H), 7.66 (d, J = 8.3 Hz, 4H), 7.01 (s, 4H), 4.03 (t, J = 6.4 Hz, 8H), (m, 8H), (m, 8H), (m, 24H), ppm (m, 12H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , 94.89, 90.39, 80.01, 79.96, 70.18, 69.90, 31.98, 31.94, 29.62, 29.48, 26.14, 26.01, 23.06, 23.02, ppm. FTIR (KBr): ν= 729, 775, 823, 997, 1028, 1163, 1213, 1217, 1388, 1411, 1467, 1492, 1600, 1701, , 2345, 2729, 2852, 2923 cm -1. EM m/z (ESI), (%I): 881 (M + Na, 10), 857 (M +, 40), 785 (30). Compound 18: Compound 8 (357 mg, mmol) and 12 (400 mg, mmol) were dissolved in dry THF (50 ml) and the system was flushed with argon. Pd(PPh 3 ) 4 (45.52 mg, mmol), CuI (7.5 mg, mmol) and i Pr 2 NH ( 0.3mL) were added. 7

9 The mixture was heating under reflux for 48 h. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed. The crude product was purified by flash chromatography on silica gel using hexane: AcOEt (9:1) as eluent. The product was obtained as yellow solid 17 ( mg, mmol). Yield 90%. M.p.: ºC. 1 H- NMR (300 MHz, CDCl 3, 25ºC): δ= 6.92 (s, 2H), 6.91 (s, 2H), 3.99 (t, J = 6.5 Hz, 4H), 3.93 (t, J= 6.3 Hz, 4H), (m, 8H), (m, 8H), (m, 16H), ppm (m, 12H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , 104, 97.8, 80, 79.9, 70.25, 69.64, 32.07, 31.94, 30.11, 29.76, 29.52, 26.24, 26.00, 23.04, 23.00, 19.10, 14.49, 14.45, ppm. EM m/z (ESI), (%I): 963 (M, 40), 95 (M +, 60), 963 (20), 877 (10). FTIR (KBr), ν: 659, 862, 945, 997, 1047, 1072, 1197, 1220, 1271, 1384, 1400, 2854, 2925, 2954 cm -1. Compound 19: Compound 4 ( mg, mmol) and 12 (697 mg, mmol) were dissolved in dry piperidine (15 ml) and the system was flushed with argon. Bis(triphenylphosphine)-palladium dichloride (25.32 mg, mmol), triphenylphosphine (18.88 mg, mmol) and copper(i) iodine (13.74 mg, mmol) were added. The mixture was stirred at room temperature for 3h. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane: CH 2 Cl 2 (10:1) as eluent. The product was obtained as a yellow solid 19 (665 mg, mmol). Yield 55%. M.p.: 58-60ºC. 1 H-NMR (200 MHz, CDCl 3, 25ºC): δ= 7.08 (s, 1H), 7.00 (s, 1H), 6.93 (s, 2H), (m, 8H), (m, 8H), (m, 8H), (m, 16H), 1.14 (brs, 21H), ppm (m, 12H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , 96.47, 90.64, 90.61, 70.09, 69.96, 69.82, 69.27, 31.67, 31.60, 31.56, 31.50, 29.69, 29.43, 29.30, 29.20, 29.17, 25.84, 25.64, 25.60, 22.57, 18.69, 14.04, 14.00, ppm. EM m/z (ESI), (%I): 863 (M + +Na, 70), 837 (M +, 20), 686 (30). 403 (30), 203 (45). FTIR (KBr), ν: 756, 908, 1647, 2252, 2399 cm -1. Compound 20: Compound 19 (308 mg, mmol) and trimethylsilylacetylene (0.16mL, mmol) were dissolved in dry THF (15 ml) and the system was flushed 8

10 with argon. Pd(PPh 3 ) 4 (45.06 mg, mmol), copper(i) iodine (7.55 mg, mmol) and diisopropylamine (0.33mL) were added. The mixture was stirred and heating at reflux during for 4 days. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane: CHCl 3 (90:1) as eluent. The product was obtained as a yellow solid 20 (306.3 g, mmol). Yield 97%. M.p: ºC. 1 H- NMR (300 MHz, CDCl 3, 25ºC): δ= 6.94 (brs, 4H), (m, 8H), (m, 8H), (m, 8H), (m, 24H), (m, 21H), (m, 12H), 0.26 ppm (s, 9H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , 96.53, 91.61, 91.22, 69.86, 69.68, 69.47, 69.27, 31.72, 31.65, 30.95, 29.74, 29.47, 29.34, 29.29, 25.89, 25.74, 25.68, 22.66, 18.74, 14.10, 14.06, 11.42, 0.00 ppm. EM m/z (ESI), (%I): 854 (M, 40), 756. FTIR (KBr): ν= 636, 769, 812, 1029, 1211, 1274, 1340, 1386, 1419, 1458, 1473, 2148, 2864, 2941 cm -1. Compound 21: Compound 20 (306.3 g, mmol) was dissolved in a mixture of THF:MeOH (1:1) 40 ml and K 2 CO 3 (49.76 mg, mmol) was added to the solution. The solution was stirred at room temperature for 2h. The mixture was extracted with dichloromethane and washed with water. The organic phase was dried with MgSO 4 and the solvent was removed under pressure. The product was purified by flash chromatography on silica gel using hexane:acoet (15:1) as eluent. The product was obtained as a yellow solid 21 ( mg, mmol). Yield 100 %. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 7.04 (s, 1H), 7.01 (s, 1H), 6.99 (s, 1H), 6.97 (s, 1H), (m, 8H), 3.35 (s, 1H), (m, 8H), (m, 8H), (m, 24H), 1.26 (brs, 3H) 1.15 (s, 18H), ppm (m, 12H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , 96.96, 92.03, 91.37, 82.67, 80.45, 78.65, 70.19, 70.09, 69.98, 69.63, 37.50, 32.10, 32.01, 31.94, 30.11, 29.84, 29.70, 29.63, 29.54, 26.27, 26.05, 26.01, 23.04, 22.99, 19.11, 14.53, 14.49, 14.44, ppm. FTIR (KBr): ν= 735, 845, 900, 1140, 1250, 1270, 1315, 1625, 2230, 3250 cm -1. EM m/z (ESI), (%I): 781 (M +, 55), 782 (M, 15), 560 (47). 9

11 Compound 22: Compound 21 (70.22 mg, mmol) and 5 (70 mg, mmol) were dissolved in dry THF (15 ml) and the system was flushed with argon. Pd(PPh 3 ) 4 (8.89 mg, 7.7 x 10-3 mmol), copper(i) iodine (1.46 mg, 7.7 x 10-3 mmol) and diisopropylamine (1 ml) were added. The mixture was refluxed for 28 h. Dichloromethane was added to the mixture and washed with saturated NH 4 Cl, HCl (10%) and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum and the crude product was purified by flash chromatography on silica gel using hexane: AcOEt (9:1) as eluent. The product was obtained as a yellow solid 22 (20 mg, mmol). Yield 64%. M.p: ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= (s, 1H), 7.84 (d, J = 8.2 Hz, 2H), 7.56 (d, J = 8.2 Hz, 2H), 6.95 (brs, 4H), (m, 8H), (m, 8H), (m, 8H), 0.9 (brs, 3H), 0.6 (brs, 21H), ppm (m, 12H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , 93.46, 90.06, 70.55, 70.18, 32.33, 31.95, 31.91, 30.10, 29.77, 29.60, 29.53, 26.10, 26.05, 23.10, 23.10, 23.03, 22.9, 18.67, 14.53, 14.43, ppm. FTIR (KBr): ν= 770, 865, 1218, 1282, 1465, 1697, 2260, 2320, 2570 cm -1. EM m/z (ESI), (%I): 885 (M+, 55), 872 (67), 746 (100), 692 (32), 606 (84), 292 (33). 2-Trimethylsilylethynyl-5-iodo-1,4-bishexyloxybenzene 23: Compound 8 (1g, mmol) was dissolved in dry THF (20mL), n-buli (2.204 mmol) was slowly added at 0 ºC. The mixture was stirring for 3 h at 0 ºC. After, I 2 (559 mg, mmol) solution in dry THF (10 ml) was added and stirring for 12 h at room temperature. The mixture was washed with Na 2 S 2 O 3, NaCl and the organic phase was dried with MgSO 4. The solvent was removed under pressure and the crude product was purified by flash chromatography on silica gel using hexane as eluent. The product was obtained as white solid 23 (1.763 mmol). Yield 80%. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 7.25 (s, 1H), 6.83 (s, 1H), (m, 4H), (m, 4H), (m, 4H), (m, 4H), (m, 6H), 0.25 ppm (s, 9H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , 99.82, 88.30, , 32.00, 31.89, 30.11, 29.67, 29.53, 26.14, 26.07, 23.04, 23.00, 14.48, 14.45, 0.34 ppm. FTIR (KBr): ν= 761, 808, 1205, 1375, 1460, 2153 cm -1. EM m/z (EI), (%I): 500 (M, 100), 442 (67), 330 (55). 10

12 Compound 24: Compound 16 (150 mg, mmol) was dissolved in a mixture of THF:MeOH (1:1) (40 ml) and K 2 CO 3 ( mg, mmol) was added to the solution. The solution was stirred at room temperature for 2 h. The mixture was extracted with dichloromethane and washed with water (2 x 50 ml). The organic phase was dried with MgSO 4. The solvent was removed under vacuum and the product was purified by flash chromatography on silica gel hexane:acoet (15:1) as eluent to afford 24 as yellow solid. Yield 100%. Compound 22 (150 mg, mmol) was dissolved in THF (40 ml) and tetrabutylammonium fluoride (0.186 mmol) was added to the solution. The solution was stirred at room temperature for 1 h. The mixture was extracted with dichloromethane and washed with water (2 x 50 ml). The organic phase was dried with MgSO 4. The solvent was removed under vacuum and the product was purified by flash chromatography on silica gel using hexane:acoet (15:1) as eluent to afford 24 as yellow solid. Yield 90 %. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= (s, 1H), 7.87 (d, J = 8.07 Hz, 2H), 7.64 (d, J=8.04 Hz, 2H), (m, 4H), 4.22 (t, J = 5.4 Hz, 8H), 3.36 (s, 1H), (m, 8H), (m, 8H), (m, 16H), ppm (m, 12H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , ,153.85,153.72, , , , , , , , , , , , 94.35, 92.35, 91.75, 90.69, 82.84, 80.41, 70.09, 69.97, 69.87, 32.01, 31.94, 30.12, 29.70, 29.65, 29.54, 26.17, 26.06, 23.06, 23.O, ppm. FTIR (KBr): ν= 733, 856, 950, 1130, 1210, 1470, 1578, 1645, 2230 cm -1. EM m/z (ESI), (%I): 840 (M +, 70), 619 (80), 413 (30). General procedure for the preparation of exttf-oppe dyad 26a-b : Dyad 26a: 4- Ethynylbenzaldehyde 6 (30.84 mg, mmol) and compound 25 (80 mg, mmol) was dissolved in dry piperidine (10 ml) then the system was flushed with argon. Bis(triphenylphosphine)-palladium dichloride (2.8 mg, mmol), triphenylphosphine (1.16 mg, 0.004mmol) and copper (I) iodine (1 mg, mmol) were added. The mixture was stirred at room temperature for 24 h. Dichloromethane was added to the residue and washed with saturated NH 4 Cl, water and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography on silica gel using hexane:ch 2 Cl 2 (3:1) to afford 26a as red solid (210 mg, mmol). Yield 85%. Mp ºC. 1 H- 11

13 NMR (CDCl 3, 300 MHz, 25 ºC): δ= (s, 1H), 7.88 (brs, 1H), (m, 2H), (m, 5H), (m, 2H), 6.30 ppm (s, 4H). 13 C-NMR (CDCl 3, 75 MHz, 25ºC): δ= , , , , 135.3, , , , , , , , , , , , , , , , , , , , 93.96, ppm. FTIR(KBr): ν= 640, 669, 754, 1163, 1259, 1458, 1508, 1546, 1600, 1607, 1697, 2923 cm -1. UV/vis (CH 2 Cl 2 ): λ max : 230, 332, 363, 387, 445 nm. MS (ESI): m/z (%): 508 (100) [M + ], 406 (12), 254 (12). Anal. Cacld for C 29 H 16 OS 4 : %C: 68.47, %H: Found: %C: 69.53, %H: Dyads 26b-c: Compound 25 ( mg, mmol) and compound 14 (100 mg, mmol) were dissolved in dry THF (30 ml) and the system was flushed with argon. Tetrakis(triphenylphosphine)-palladium (6.4 mg, 5.53x10-3 mmol), copper (I) iodine (84.9 mg, x10-3 mmol) and diisopropylamine (1mL) were added to the solution. The mixture was refluxed for 3h (26b) and 48 h (26c). The mixture was extracted with dichloromethane and washed with NH 4 Cl, water and NaCl. The organic phase was dried with MgSO 4 and the solvent was removed under vacuum. The solid was purified by flash chromatography on silica gel. Dyad 26b: Eluent: hexane:ch 2 Cl 2 (3:1). 26b was obtained as red solid 115 (94.3 g, 0.11 mmol). Yield 50 %. Mp ºC. 1 H-NMR (300 MHz, CDCl 3, 25 ºC): δ= (s, 1H), 8.46 (d, J = 1.51 Hz, 1H), (m, 3H), (m, 4H), (m, 3H), 7.08 (s, 1H), 7.06 (s, 1H), 6.95 (brs, 4H), (m, 4H), (m, 4H), (m, 4H), (m, 8H), ppm (m, 6H). 13 C-NMR (75 MHz, CDCl 3, 25 ºC): δ= , , , , , , , , , , , , , , , , , , 129.0, , , , , , , (CH), , , 76.43, 76.02, 75.63, 70.04, 69.98, 31.99, 30.11, 29.66, 26.17, 23.07, ppm. FTIR (KBr): ν= 669, 756, 1215, 1467, 1488, 1508, 1600, 1701, 2343, 2360, 2931, 2958, 3018 cm -1. MS (ESI): m/z (%): 809 (15) [M + ], 808 (M +, 88), 707 (75), 637 (10). UV/vis (CH 2 Cl 2 ) : λ max : 446, 402, 317, 228 nm. Anal. Calcd for C 49 H 44 O 3 S 4 : %C: 72.74, %H: Found: %C: 72.80, % H: Dyad 26c: Eluent:hexane: CH 2 Cl 2 (1:1). 26c was obtained as a yellow solid (94.3 g, 0.11 mmol) with 38% yield. Mp: ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 12

14 10.03 (s, 1H), 7.89 (brs, 2H), (m, 5H), 7.45 (dd, J 1 = 8.09 Hz, J 2 = 1.51 Hz, 1H), (m, 2H), 7.04 (brs, 4H), 6.33 ppm (d, J = 4.5 Hz, 4H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 95.86, 94.29, 92.50, 91.67, 90.75, 86.67, 70.16, 70.08, 69.90, 32.33, 32.12, 32.04, 32.01, 30.76, 30.11, 29.84, 29.70, 26.27, 26.17, 26.09, 23.39, 23.10, 23.06, 14.55, ppm. FTIR (KBr): ν= 756, 908, 1647, 2252, 2399 cm -1. EM m/z (ESI), (%I): 1108 (M +, 70), 1008 (80), 777 (30). 685 (30). UV-vis (CH 2 Cl 2 ), λ max : 233, 277, 309, 366, 412 nm. Anal. Calcd for C 69 H 72 O 5 S 4 : %C 74.69, %H Found: %C: 74.55, %H: General procedure for the preparation of exttf-oppe-c 60 triads 27a-c: [60]fullerene (85 mg, mmoles) was dissolved in chlorobenzene (ultrasound 30 min), the corresponding aldehyde N-methylglycine (1.5eqv) was added. The mixture was heated under reflux for 3 h. After the evaporation of the solvent, the residue was purified by flash chromatography on silica gel. The black solid obtained after chromatography was further purified by repeated centrifugation in methanol and diethyl ether to yield the corresponding triads 27a-c as brown solids. Compound 27a: Eluent: CS 2 :hexano (2:1). Yield 33%. Mp > 300 ºC. 1 H- NMR (300 MHz,CDCl 3, 25ºC): δ= 7.87 (brs, 2H), 7.76 (brs, 1H), (m, 5H), (m, 3H), 6.38 (d, J = 6.8 Hz, 4H), 5.09 (s, 1H), 5.05 (s, 1H), 4.38 (d, J=9.33 Hz, 1H), 2.94 ppm (s, 3H). 13 C- NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 92.15, 90.88, 83.81, 77.65, 70.62, 69.47, 40.67, ppm. FTIR(KBr): ν= 527, 1259, 1375, 1460, 2923, 2850, 3434 cm -1. UV-vis (CH 2 Cl 2 ) : λ max : 232, 255, 313, 376, 431, 444 nm. EM m/z (EI), (%I): 1255 (100) [M], 1254 [M + ]. 13

15 Compound 27b: Eluent: toluene. Yield 63%. Mp > 300 ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 8.4 (d, J = 1.5 Hz, 1H), (m, 3H), 7.90 (dd, J 1 = 8.1 Hz, J 2 = 1.65, 2H), (m, 3H), (d, J = 7.96, 2H), 7.05 (s, 1H), 7.03 (s, 1H), 6.79 (s, 4H), 5.03 (d, J =9.19 Hz, 1H), 4.98 (s, 1H), 4.30 (d, J = 9.19 Hz, 1H), (m, 4H), 2.86 (s, 3H), (m, 4H), (m, 4H), (m, 8H), ppm (m, 6H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 93.89, 91.54, 75.88, 70.02, 40.46, 39.88, 35.11, 31.95, 30.12, 29.63, 26.15, 23.04, 14.48, ppm. FTIR (KBr): ν= 527, 669, 758, 1186, 1217, 1222, 2395, 2150, 2175 cm -1. EM m/z (EI), (%I): 1554 (56)[ M + ], 1384 (35). UV-vis (CH 2 Cl 2 ), λ max : 250, 317, 384, 491 nm. Compound 27c : Eluent : chloroform. Yield 53 %. Mp > 300 ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 8.45 (brs, 1H), (m, 3H), (m, 5H), (m, 2H), 7.06 (s, 2H), 7.04 (s, 2H), 7.01 (s, 2H), 7.00 (s, 2H), 5.02 (d, J = 9.19 Hz, 1H), 4.99 (s, 1H), 4.30 (d, J = 9.19 Hz, 1H), (m, 4H), 2.85 (s, 3H), (m, 4H), (m, 4H), (m, 8H), ppm (m, 6H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 11751, , , , , , 93.87, 92.40, 91.95, 91.67, 83.64, 70.12, 70.09, 69.95, 68.55, 32.02, 31.97, 31.95, 30.11, 29.66, 26.07, 23.06, 14.49, ppm. FTIR (KBr): ν= 526, 756, 928, 1050, 2232, 2399 cm -1. EM m/z (EI), (%I): 1855 (33)[M], 1275 (50), 720 (67). UV-vis (CH 2 Cl 2 ), λ max : 494, 396, 314, 245 nm. General procedure for the preparation of reference compounds: C 60 ( mg, mmol) was dissolved in chlorobenzene (20 ml) (ultrasound 30 min), compound 9 (97 mg, mmol) and N-methylglycine (25.76 mg, mmol) were added. The 14

16 mixture was heated under reflux for 3 h. After the evaporation of the solvent, the residue was purified by column chromatography on silica gel. Compound 28: Eluent: Chloroform. Yield 43 %. Mp > 300 ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 7.80 (brs, 2H), 7.60 (d, J = 8.51 Hz, 2H), 6.93 (s, 2H), 5.00 (d, J = 9.33 Hz, 1H), 4.96 (s, 1H), 4.29 (d, J = 9.47 Hz, 1H), (m, 4H), 2.83 (s, 3H), (m, 4H), (m, 4H), (m, 8H), (m, 6H), 0.26 ppm (s, 9H). 13 C-NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,142.94, , , , , , , , , , , , , , , , , , , , , , , , , , , 94.99, 87.04, 83.69, 70.41, 69.93, 69.82, 69.44, 40.44, 32.02, 31.98, 29.68, 29.64, 26.10, 23.05, 14.51, 0.36 ppm. FTIR (KBr): ν= 526, 553, 574, 758, 842, 1161, 1215, 1247, 1377, 1409, 1463, 1490, 1508, 2150, 2779, 2854, 2925, 2949 cm -1. EM m/z (ESI), (%I): 1249 (M, 40), 1248 (M +, 35), 1024 (10), 924 (23), 817 (8). UV-vis (CH 2 Cl 2 ), λ max : 253, 312, 357 nm. Compound 29: Eluent: Chloroform. Yield 60%. Mp > 300 ºC. 1 H-NMR (300 MHz, CDCl 3, 25ºC): δ= 7.81 (brs, 2H), (m, 2H), 6.87 (brs, 4H), 5.02 (d, J = 9.03 Hz, 1H), 4.98 (s, 1H), 4.30 ( d, J = 9.42 Hz, 1H), (m, 8H), 2.86 (s, 3H), (m, 8H), (m, 8H), (m, 16H), ppm (m, 12H). 13 C- NMR (75 MHz, CDCl 3, 25ºC): δ= , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 83.75, 77.23, 76.73, 76.28, 74.94, 73.91, 73.12, 69.94, 69,83, 69.75, 69.54, 31.54, 31.51, 29.67, 29.18, 29.14, 29.09, 25.63, 25.59, 22.60, 22.57, 18.67, 18.64, 17.76, 16.22, 16.02, 15.74, ppm. FTIR (KBr): ν: 526, 660, 745, 800, 1126, 1310, 1645, 2255 cm -1. UV-vis (CH 2 Cl 2 ), λ max : 230, 255, 317, 380, 397 nm. EM m/z (MALDI-TOF): 1290 [M + ]. 15

17 Figure S1. Electrostatic potential as calculated by AM1 CIS for the ground and chargeseparated states of 27a-c. The positive charge is represented in red and the negative in blue. 16

18 Stabilization of CT States by Solvent and Geometrical Relaxation Single-point calculations on the relaxed structures of the ground and excited states in the simulated solvents hexane (ε=2.023), CCl 4 (ε=2.229), benzene (ε=2.274), ether (ε=4.197), chloroform (ε=4.806), methylene chloride (ε=8.930), pyridine (ε=12.40), acetone (ε=20.56), ethanol (ε=24.55) nitrobenzene (ε=43.82), acetonitrile (ε=35.94) and dimethyl sulfoxide (ε=46.45) were performed in order to judge the solvent effects on the relative stabilities of the different states for 27a-c. Figure S2. Dependence of the calculated heats of formation, H f, for the discussed states of 27c on solvent permittivity: ground state (circles), local excited state (triangles), BCT (squares), CT (rotated squares). Figure S2 shows the dependence of the calculated heats of formation, H f, of the discussed states of 27c on solvent permittivity ((ε-1/(2ε+1)). By optimizing the localexcited (LE) state, the BCT state and the CT state of 27c, it was possible to determine the energy levels of the three different Franck-Condon states and get more insight into the electron-transfer pathway. The calculations reveal that the relative energies of the different states and conformations and their solvent dependence are reproduced remarkably well in accordance with the experimental trends. As illustrated in Figure S2, with higher solvent polarity the energy splitting between the different states increases significantly whereas their relative energies decrease due to solvent stabilization. Equally important, one can see that the BCT becomes more and more accessible as the polarity of the solvent increases. This behavior was also observed in the photophysical 17

19 experiments. However, no crossing between the CT and BCT state, even in nonpolar media, was observed during the calculations. The results for the monomer 27a and the dimer 27b reveal equal solvent dependence of the discussed states. However, in these two compounds no BCT is present. The heat of formation of the CT states is increasing almost linearly from monomer to trimer. These trends prove the observations resulting from the photophysical measurements and confirm the suggested charge-transfer behavior of the C 60 -oppe-exttf. Thus, the calculations support the hypothesis that in all solvents an excitation of the triad results in the CT state, which supports our interpretation of the electron-transfer mechanism. Calculating the Coulson charge on exttf and C 60 gives a value of 1.0 e - and -1.1 e -, respectively, for all the triads, indicating complete transfer of one electron from the donor to the acceptor with some delocalization of the positive charge (4.6 %) into the bridge. ExTTF is clearly oxidized with the positive charge localized on the sulfur atoms (0.6 e - ), whereas C 60 is reduced with the charge being delocalized throughout the carbon cage. This confirms the one-electron charge transfer from donor to acceptor. References [S1] Stockmann, Kurzawa, Fritz, Acar, Schneider, Daub, Engl, Clark, J. Phys. Chem A 2002, 106, [S2] Dewar, M. J. S.; Zoebisch, E.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, Holder, A. J. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer, H. F., III, Schreiner, P. R., Eds.; Wiley: Chichester, 1998; Vol. 1, p 8 [S3] Dewar, M. J. S.; Liotard, D. A. J. Mol. Struct. (THEOCHEM) 1990, 206, 123 [S4] Bondi, A. J. Phys. Chem. 1964, 68, 441 [S5] Local molecular properties and their use in predicting reactivity, B. Ehresmann, B. Martin, A. H. C. Horn and T. Clark, J. Mol. Model. 2003, 9, ; QSAR and QSPR based solely on surface properties?, T. Clark, J. Mol. Graph. Model. 2004, 22,

20 [S6] T. Clark, Jr-H. Lin, A. H. C. Horn, Parasurf 07Cepos InSilico Ltd., Ryde, UK, 2007 ( [S7] H. Lanig, R. Koenig, T. Clark, Tramp 1.1d

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Supporting Information

Supporting Information S1 Supporting Information Synthesis, Characterization, and Photophysical properties of a melamine-mediated hydrogenbonded phthalocyanine-perylenediimide assembly Ángel J. Jiménez,, Rafael Krick Calderón,

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z50567 Wiley-VCH 2003 69451 Weinheim, Germany Metallacarborane-Based Nanostructures: A Carbon-Wired Planar Octagon** Haijun Yao, Michal Sabat, and Russell

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,

More information

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and

More information

Supplementary Information

Supplementary Information Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

Supporting Information

Supporting Information Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Negishi reaction in BODIPY dyes. Unprecedented alkylation by palladium-catalyzed

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 ph-controlled Reversible Formation of a Supramolecular Hyperbranched Polymer Showing Fluorescence Switching Bingran

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Effect of polymer chain conformation on field-effect transistor performance: synthesis and properties of two arylene imide based D-A copolymers Dugang Chen, a Yan Zhao,

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Concise Stereoselective Synthesis of ( )-Podophyllotoxin by Intermolecular Fe III -catalyzed Friedel-Crafts Alkylation Daniel Stadler, Thorsten

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,

More information

How to build and race a fast nanocar Synthesis Information

How to build and race a fast nanocar Synthesis Information How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,

More information

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric Supplementary Information for Stable Supramolecular Helical Structure of C 6 -Symmetric Hydrogen-Bonded Hexakis(phenylethynyl)benzene Derivatives with Amino Acid Pendant Groups and Their Unique Fluorescence

More information

Supporting Information

Supporting Information Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook

More information

Accessory Information

Accessory Information Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department

More information

Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)

Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and

More information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL

More information

Supporting Information:

Supporting Information: Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:

More information

Electronic supplementary information. Strong CIE activity, multi-stimuli-responsive fluorescence and data

Electronic supplementary information. Strong CIE activity, multi-stimuli-responsive fluorescence and data Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Electronic supplementary information Strong CIE activity, multi-stimuli-responsive

More information

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted

More information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for

More information

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,

More information

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic

More information

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,

More information

Supplementary Information

Supplementary Information Supplementary Information J. Braz. Chem. Soc., Vol. 26, No. 4, S1-S16, 2015. Printed in Brazil - 2015 Sociedade Brasileira de Química 0103-5053 $6.00+0.00 SI Jaqueline P. Vargas, a Lucimar M. Pinto, b

More information

Supporting Information

Supporting Information Supporting Information Selective Synthesis of [6]-, [8]-, and [10]Cycloparaphenylenes Eiichi Kayahara, 1,2 Takahiro Iwamoto, 1 Toshiyasu Suzuki, 2,3 and Shigeru Yamago* 1,2 1 Institute for Chemical Research,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Supporting Information

Supporting Information Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and

More information

Chia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*

Chia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen* Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization

More information

Facile Multistep Synthesis of Isotruxene and Isotruxenone

Facile Multistep Synthesis of Isotruxene and Isotruxenone Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw

More information

Supporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra

Supporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra Supporting Information for Sonogashira Hagihara reactions of halogenated glycals Dennis C. Koester and Daniel B. Werz* Address: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität

More information

Multistep Electron Transfer Systems Based. on Silicon Phthalocyanine, [60]Fullerene and. Trinitrofluorenone

Multistep Electron Transfer Systems Based. on Silicon Phthalocyanine, [60]Fullerene and. Trinitrofluorenone Supporting Information Multistep Electron Transfer Systems Based on Silicon Phthalocyanine, [60]Fullerene and Trinitrofluorenone Luis Martín-Gomis, a Kei hkubo, b Fernando Fernández-Lázaro, a Shunichi

More information

dichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere.

dichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere. Supporting Information Experimental The presence of atropisomerism arising from diastereoisomerism is indicated in the 13 C spectra of the relevant compounds with the second isomer being indicated with

More information

Supporting Information

Supporting Information Intramolecular hydrogen-bonding activation in cysteines. New effective radical scavenging Luisa Haya, a Iñaki Osante, b Ana M. Mainar, a Carlos Cativiela, b Jose S. Urieta*,a a Group of Applied Thermodynamics

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ES) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Supporting nformation for BODPY-Containing

More information

Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot

Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot Laure-Emmanuelle Perret-Aebi, Alexander von Zelewsky 1, Christiane Dietrich- Buchecker and Jean-Pierre Sauvage Bis-5,6-pinene

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION S1 SUPPORTING INFORMATION FIRST STEREOSELECTIVE SYNTHESIS OF (-)-SIPHONODIOL AND (-)-TETRAHYDROSIPHONODIOL, BIOACTIVE POLYACETYLENES FROM MARINE SPONGES Susana López,* Francisco Fernández-Trillo, Pilar

More information

Supplementary Material. Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction

Supplementary Material. Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction Supplementary Material Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction Silvia M. Barolo, Sandra E. Martín,* Roberto A. Rossi* INFIQC, Departamento de Química Orgánica,

More information

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro

More information

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Supplementary Information

Supplementary Information Supplementary Information Supramolecular polymerization of hydrogen-bonded rosettes with anthracene chromophores: regioisomeric effect on nanostructures Deepak D. Prabhu, Keisuke Aratsu, Mitsuaki Yamauchi,

More information

Triazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3

Triazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3 Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,

More information

Ring-Opening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols

Ring-Opening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols Ring-pening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols Jumreang Tummatorn, and Gregory B. Dudley, * Department of Chemistry and Biochemistry, Florida State University,

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS OF A 3-THIOMANNOSIDE Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,

More information

Highly stereocontrolled synthesis of trans-enediynes via

Highly stereocontrolled synthesis of trans-enediynes via Supporting Information for Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes Tsutomu Konno*, Misato Kishi, and Takashi Ishihara Address: Department of Chemistry

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 Paraldehyde as an Acetaldehyde Precursor in Asymmetric Michael Reactions Promoted by Site-Isolated Incompatible Catalysts

More information

Preparation and ring-opening reactions of N- diphenylphosphinyl vinyl aziridines

Preparation and ring-opening reactions of N- diphenylphosphinyl vinyl aziridines Supporting Information for Preparation and ring-opening reactions of N- diphenylphosphinyl vinyl aziridines Ashley N. Jarvis 1, Andrew B. McLaren 1, Helen M. I. Osborn 1 and Joseph Sweeney* 1,2 Address:

More information

Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.

Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Tetrahedron Letters 1 Pergamon TETRAHEDRN LETTERS Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Jennifer L. Stockdill,

More information

Supporting Information

Supporting Information Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a

More information

Supplementary Material

Supplementary Material 10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination

More information

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry

More information

Supporting Information

Supporting Information Supporting Information Towards Singlet Oxygen Delivery at a Measured Rate: A Selfreporting Photosensitizer Sundus Erbas-Cakmak #, Engin U. Akkaya # * # UNAM-National Nanotechnology Research Center, Bilkent

More information

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs)

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs) Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 27 Electronic Supplementary Information bis-zn II salphen complexes bearing pyridyl functionalized

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:

More information

A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media

A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Supplementary Information A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Weiwei Wang and Quanrui Wang* Department of Chemistry,

More information

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School

More information

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12 Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry

More information

Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition

Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Sonia Amel Diab, Antje Hienzch, Cyril Lebargy, Stéphante Guillarme, Emmanuel fund

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Proof of Principle for a Molecular 1:2 Demultiplexer to Function as an Autonomously Switching Theranostic Device Sundus Erbas-Cakmak, Ozgur Altan Bozdemir, Yusuf Cakmak,

More information

BODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage

BODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 BODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage Tugba Ozdemir

More information

Appendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized

Appendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Appendix A Supplementary Information Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi

More information

Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts

Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPORTING INFORMATION Synthesis of Functionalized Thia Analogues of Phlorins and Covalently Linked Phlorin-Porphyrin Dyads Iti Gupta a, Roland Fröhlich b and Mangalampalli Ravikanth *a a Department of

More information

Supporting Information

Supporting Information Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and

More information

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,

More information

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B Supporting Information Expeditious Construction of the DEF Ring System of Thiersinine B Masaru Enomoto and Shigefumi Kuwahara* Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural

More information

Supporting Information

Supporting Information 1 A regiodivergent synthesis of ring A C-prenyl flavones Alberto Minassi, Anna Giana, Abdellah Ech-Chahad and Giovanni Appendino* Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using

More information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water Dong-Hwan Lee, Ji-Young Jung, and Myung-Jong

More information

A Triangular Macrocycle Altering Planar and Bulky Sections in Its Molecular Backbone

A Triangular Macrocycle Altering Planar and Bulky Sections in Its Molecular Backbone Supporting Information A Triangular Macrocycle Altering Planar and Bulky Sections in Its Molecular Backbone Jiří Kaleta and Ctibor Mazal* Department of Chemistry, Faculty of Science, Masaryk University,

More information

Supporting Information

Supporting Information Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of

More information

Supporting Information For:

Supporting Information For: Supporting Information For: Highly Fluorinated Ir(III)- 2,2 :6,2 -Terpyridine -Phenylpyridine-X Complexes via Selective C-F Activation: Robust Photocatalysts for Solar Fuel Generation and Photoredox Catalysis

More information

Supporting Online Material

Supporting Online Material Supporting Online Material Topology Guided Design and Syntheses of Highly Stable Mesoporous Porphyrinic Zirconium MOFs with High Surface Area. Tian-Fu Liu, a Dawei Feng, a Ying-Pin Chen, a,b Lanfang Zou,

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some

More information

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Seyoung Choi and Sangho Koo* Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. E-mail:

More information

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol.

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol. SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Diphenylprolinol Silyl Ether in Enantioselective, Catalytic Tandem Michael-Henry Reaction for the Control of Four Stereocenters Yujiro Hayashi*,

More information

A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour

A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour Eyad

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

hydroxyanthraquinones related to proisocrinins

hydroxyanthraquinones related to proisocrinins Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,

More information

Supporting Information

Supporting Information Supporting Information Reversible Microwave-Assisted Cycloaddition of Aziridines to Carbon Nanotubes Fulvio G. Brunetti, a,b M. Antonia Herrero, a,b Juan de M. Muñoz, b Silvia Giordani, a Angel Díaz-Ortiz,

More information

Supplementary Information (Manuscript C005066K)

Supplementary Information (Manuscript C005066K) Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION Synthesis and Biological Evaluation of 2-Methyl-4,5-Disubstituted Oxazoles as a Novel Class of Highly Potent Antitubulin Agents Romeo Romagnoli, 1 * Pier Giovanni Baraldi, 1 Filippo Prencipe, 1 Paola Oliva,

More information

Electronic Supplementary Information. Highly Efficient Deep-Blue Emitting Organic Light Emitting Diode Based on the

Electronic Supplementary Information. Highly Efficient Deep-Blue Emitting Organic Light Emitting Diode Based on the Electronic Supplementary Information Highly Efficient Deep-Blue Emitting rganic Light Emitting Diode Based on the Multifunctional Fluorescent Molecule Comprising Covalently Bonded Carbazole and Anthracene

More information

Supporting Information. For. Organic Semiconducting Materials from Sulfur-Hetero. Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical

Supporting Information. For. Organic Semiconducting Materials from Sulfur-Hetero. Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical upporting Information For Organic emiconducting Materials from ulfur-hetero Benzo[k]fluoranthene Derivatives: ynthesis, Photophysical Properties and Thin Film Transistor Fabrication Qifan Yan, Yan Zhou,

More information

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2012 Supplementary data Cu-catalyzed in situ generation of thiol using xanthate as thiol

More information

Water-Compatible Highly Active Reusable PEG-Coated Mesoporous Silica. Supported Palladium Complex and Its Application in Organic Synthesis

Water-Compatible Highly Active Reusable PEG-Coated Mesoporous Silica. Supported Palladium Complex and Its Application in Organic Synthesis Water-Compatible Highly Active Reusable PEG-Coated Mesoporous Silica Supported Palladium Complex and Its Application in Organic Synthesis Qing Yang a, b, Shengming Ma,* a and Jixue Li, b Feng-shou Xiao,*

More information

Halogen halogen interactions in diiodo-xylenes

Halogen halogen interactions in diiodo-xylenes Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002 Supporting Information for Angew. Chem. Int. Ed. Z19663 Wiley-VCH 2002 69451 Weinheim, Germany Selective Measurements of a itroxide-itroxide Distance of 5 nm and a itroxide-copper distance of 2.5 nm in

More information

Facile Synthesis of Flavonoid 7-O-Glycosides

Facile Synthesis of Flavonoid 7-O-Glycosides Facile Synthesis of Flavonoid 7-O-Glycosides Ming Li, a Xiuwen Han, a Biao Yu b * a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China

More information