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1 Supporting Information Title:General Synthetic Approach towards Geminal-Substituted Tetraarylethene Fluorophores with Tunable Emission Properties: X-Ray Crystallography, Aggregation-Induced Emission and Piezofluorochromism Guo-Feng Zhang, Hongfeng Wang, Matthew P. Aldred,*, Tao Chen, Ze-Qiang Chen, Xianggao Meng* and Ming-Qiang Zhu* Wuhan National Laboratory for ptoelectronics, School of ptical and Electronic Information, Huazhong University of Science and Technology, Wuhan, Hubei , China. Department of Chemistry, Durham University, South Road, Durham, UK, DH1 3LE. Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei , China. 1
2 1. Experimental. (a) Instrumentation. All commercially available starting materials, reagents and solvents were used as supplied, unless otherwise stated, and were purchased from Energy, alfa aesar, J&K and Zhengzhou Huawen Chemical Co. Ltd. All reactions were carried out under a dry nitrogen atmosphere and the temperatures were measured externally. Toluene and tetrahydrofuran (THF) were dried using sodium wire and benzophenone as the indicator. Reported yields are isolated yields. Purification of all final products was accomplished by gravity column chromatography, using silica gel. For qualitative purity tests of all intermediates and final products, a single spot (visualised using UV-light at 254 nm and 365 nm) was obtained. The UV-Vis absorption and photoluminescence emission of the compounds were recorded on Shimadzu UV-VIS-NIR Spectrophotometer (UV-3600) and Edinburgh instruments (FLS 920 spectrometers), respectively. The thermal analysis of these synthesized compounds was carried out on a Pyris1 TGA (PerkinElmer Instruments) thermogravimetric analyzer thermogravimetric analyzer under nitrogen atmosphere with the heat rate at 10 o C/min. The scanning electron microscopy pictures were performed on FEI Nova NanoSEM 450. The relative fluorescence quantum yields were estimated using 9,10-diphenylanthracene in cyclohexane as standard material. The NMR spectra were recorded on a 400 MHz instrument using CDCl 3 or CD 2 Cl 2 as the solvents. The Mass Spectrometry was recorded on matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TF) using Cyano-4-hydroxycinnamic Acid (CHCA) as the matrix or Agilent (1100 LC/MSD Trap). The related precursors of (9-methyl-9H-carbazol- 3-yl)boronic acid 1, anthracen-9-yl boronic acid 2, (4-(1,2,2-triphenylvinyl)phenyl)boronic acid 3, 2-(2,6-diisopropylphenyl)-6-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-benzo[de]isoquinoline-1,3(2h)-dione 4, 3,3-diphenyl- 2-(4-(4,4,5,5-tetramethyl-1,3, 2-dioxaborolan -2-yl)phenyl) acrylonitrile 5, 1,1-dibromo-2,2-diphenylene 6 was synthesized according to the literature published. 2
3 (b) Synthetic procedures. For the synthesis of geminal-taes CBr 4, PPh 3 Br Br Suzuki / Stille couplings R R Toluene N R: S CN N A example of asymmetric synthesis of TAEs Br Br B(H) 2 B(H) 2 and Suzuki couplings TPMAn Scheme S1 The synthesis of TAE compounds Synthetic procedures: Scheme S2 McMurry reaction for the synthesis of TPE-H Scheme S3 The synthesis of the precursors for compound DPDNI Synthesis of 6-bromo-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 4 A mixture of 6-bromobenzo[de]isochromene-1,3-dione (10g, 36.1mmol), 2,6-diisopropylaniline (6.40 g, 36.1 mmol) in acetic acid (150 ml) was heated to reflux for 3 days. The precipitate was filtered, washed with water and ethanol, and then dried in the oven to afford the off-white solid (14.9 g, 94.6 % yield). 3
4 1 HNMR (400 MHz, CDCl 3 ): δ (ppm) 8.71 (d, J = 7.2 Hz, 1H), 8.65 (d, J = 8.4 Hz, 1H), 8.47 (d, J = 7.6 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.89 (t, J = 8.4 Hz, 1H), 7.46 (t, J = 7.6 Hz, 1H), 7.31 (d, J = 8.0 Hz, 2H), 2.66 (m, 2H), 1.14 (d, J = 6.8 Hz, 12H). Synthesis of 2-(2,6-diisopropylphenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1Hbenzo[de]isoquinoline-1,3(2H)-dione 4 A mixture of 6-bromo-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (4.36 g, 10mmol), bis(pinacolato)diborane (3.81 g, 15 mmol), potassium acetate (2.93 g, 30 mmol) in 50 ml anhydrous dioxane which was freshly distilled was heated to 90 o C overnight under nitrogen. n cooling to room temperature, the solvent was removed and the residue was purified by column chromatography using DCM/PE (7:3 v/v) as the eluent to afford the product (2.35 g, 48.6% yield). 1 HNMR (400 MHz, CDCl 3 ): δ (ppm) 9.20 (d, J = 8.4 Hz, 1H), 8.65 (d, J = 7.2 Hz, 1H), 8.62 (d, J = 7.2 Hz, 1H), 8.34 (d, J = 7.2 Hz, 1H), 7.81 (t, J = 7.6 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.31 (d, J = 8.0 Hz, 2H), 2.70 (m, 2H), 1.47 (s, 12H), 1.14 (d, J = 6.8 Hz, 12H). MS (APCI): m/z [(M+1) + ] Scheme S4 The synthesis of the precursors for compound DPDTAN 2-(4-Bromophenyl)-3,3-diphenylacrylonitrile: 5 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 7.42 (m, 5H), 7.35 (d, J = 8.0 Hz, 2H), 7.25 (m, 1H), 7.19 (t, J = 7.2 Hz, 2H), 7.11 (d, J = 8.4 Hz, 2H), 6.98 (d, J = 8.4 Hz, 2H). MS (APCI): m/z [(M+1) + ] (4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile. 5 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 7.62 (d, J = 8.4 Hz, 2H), 7.42 (m, 5H), 7.27 (m, overlapping with solvent peak, 3H), 7.15 (t, J = 7.2 Hz, 2H), 6.98 (d, J = 8.4 Hz, 2H), 1.37 (s, 12H). MS (APCI): m/z [(M+1) + ] Scheme S5 Corey-Fuchs reaction for 1,1-dibromo-2,2-diphenylene 6 Typically, A mixture of benzophenone (3.04 g, mmol), carbon tetrabromide (11.06 g, mmol), and triphenyl phosphine (17.53 g, mmol) in 250 ml of anhydrous toluene was run at 140 o C for 4 days. n cooling to room temperature, the mixture was filtered, washed with toluene and the filtrate was collected, washed with water. The organic layer was separated, dried with Na 2 S 4, and then the solvent was removed by rotary evaporator. After the residue was purified by column chromatography on silica gel using hexane as the eluent, the product was recrystallized in ethanol to afford 4.91 g of 1,1-dibromo-2,2-diphenylene as a light yellow needle-like crystalline solid (87.1% yield). 1 HNMR (CDCl 3, 400 MHz) δ (ppm): (m, 10H). 13 CNMR (CDCl 3, 100 MHz) δ (ppm): , , , , ,
5 Scheme S6 Stille coupling for 2,2'-(2,2-diphenylethene-1,1-diyl)dithiophene (DPDT) A mixture of 1,1-dibromo-2,2-diphenylethene (0.34 g, 1 mmol), 2-(Tributylstannyl)thiophene (1.12 g, 3 mmol), Pd(PPh 3 ) 4 (58 mg, 0.05 mmol), tetrabutylammonium hydrogen sulfate (34 mg, 0.1 mmol), K 2 C 3 (14 mg, 0.1 mmol) in toluene (20 ml) and water (10 ml) was heated to 90 o C and stirred under nitrogen overnight. After cooling down to room temperature, the organic layer was separated and the water layer was extracted with dichloromethane (DCM). The combined organic solution was dried with Na 2 S 4 for several hours. After filtration, the resulting solution was concentrated by rotary evaporator. The residue was purified by column chromatography on silica gel using DCM/PE (v/v: 1:9) as the eluent to obtain the DPDT (0.22 g, 63.9%). 1 HNMR (CD 2 Cl 2, 400 MHz) δ (ppm): (m, 12H), 6.82 (t, 2H), 6.83 (m, 2H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , , , MADLI-TF: found: Scheme S7 Suzuki coupling for 1,1'-(2,2-diphenylethene-1,1-diyl)dinaphthalene (DPDN 1 ) The same synthetic procedure described in Scheme S6 was performed for compound DPD N 1, and the residue was purified by column chromatography on silica gel using DCM/PE (v/v: 3:7) as the eluent to obtain the DPDN 1 (64.8%, yield) as a white powder. 1 HNMR (CD 2 Cl 2, 400 MHz) δ (ppm): (m, 18H), (dd, J = 8.0 Hz and J = 7.2 Hz, 4H), 8.25 (d, J = 7.4 Hz, 1H), 8.50 (d, J = 8.0 Hz, 1H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , , , , , , , , , , , , , MADLI-TF: found: Scheme S8 Suzuki coupling for 2,2'-(2,2-diphenylethene-1,1-diyl)dinaphthalene (DPDN 2 ) The same synthetic procedure described in Scheme S6 was performed for compound DPD N 2 and the residue was purified by column chromatography on silica gel using DCM/PE (v/v: 3:7) as the eluent to obtain the DPDN 2 (71.5%, yield) as a white powder. 1 HNMR (CD 2 Cl 2, 400 MHz) δ (ppm): (m, 10H), 7.24 (d, J = 8.8 Hz, 2H), (m, 4H), (m, 6H), 7.76 (d, J = 8.0 Hz, 2H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , , , , , MADLI-TF: found: Scheme S9 9,9'-(2,2-diphenylethene-1,1-diyl)dianthracene (DPDAn) 5
6 The same synthetic procedure described in Scheme S6 was performed for compound DPDAn and the residue was purified by column chromatography on silica gel using DCM/PE (v/v: 1:4) as the eluent to obtain the DPDAn (62.3%, yield) as a yellow powder. 1 HNMR (CD 2 Cl 2, 400 MHz) δ (ppm): (b, 4H), 8.35 (s, 2H), 7.91 (d, J = 8.8 Hz, 4H), (m, 12H), 6.86 (m, 6H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , MADLI-TF: found: Scheme S10 3,3'-(2,2-diphenylethene-1,1-diyl)bis(9-methyl-9H-carbazole) (DPDCz) The same synthetic procedure described in Scheme S6 was performed for compound DPDCz and the residue was purified by column chromatography on silica gel using DCM/PE (v/v: 2:8) as the eluent to obtain the DPDCz (69.3%, yield) as a white powder. 1 HNMR (CD 2 Cl 2, 400 MHz) δ (ppm): 7.88 (m, 4H), 7.49 (t, J = 8.0 Hz, 2H), 7.40 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 8.4 Hz, 2H), 7.11 (m, 14H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , , , , , , , , MADLI-TF: found: Scheme S11 2,2'-((2,2-diphenylethene-1,1-diyl)bis(4,1-phenylene))bis(3,3-diphenylacrylonitrile) (DPDTPAN) The same synthetic procedure described in Scheme S6 was performed for compound DPDTPAN and the residue was purified by column chromatography on silica gel using DCM/PE (v/v: 5:5) as the eluent to obtain the DPDTPAN (68.4%, yield) as a yellow powder. 1 HNMR (CD 2 Cl 2, 400 MHz) δ (ppm): 6.90 (d, J = 8.4 Hz, 3H), (m, 24H), 7.19 (m, 11H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , MADLI-TF: found: Br Br B(H) 2 Suzuki couplings Scheme S12 synthesis of DPDTPE The same synthetic procedure described in Scheme S6 was performed for compound DPDTPE, however, the product was precipitated in toluene. After filtered, the solid was redisolved in hot chloroform, and then column chromatography was carried out to remove the Pd catalyst on silica gel using DCM as the eluent to obtain the DPDTPE (78.6%, yield) as a white powder. 1 HNMR 6
7 (CDCl 3, 400 MHz) δ (ppm): 6.69 (m, 8H), (m, 40H). 13 CNMR (CDCl 3, 100 MHz) δ (ppm): , , , , , , , , , , , , , , , MADLI-TF: found: Br Br N B N N Suzuki couplings Scheme S13 6,6'-(2,2-diphenylethene-1,1-diyl)bis(2-(2,6-diisopropylphenyl)-1H-benzo [de]isoquinoline-1,3(2h)-dione) (DPDNI) The same synthetic procedure described in Scheme S6 was performed for compound DPDNI and the residue was purified by column chromatography on silica gel using EA/PE (v/v: 1:4) as the eluent to obtain the DPDNI (60.2%, yield) as a yellow powder. 1 HNMR (CD 2 Cl 2, 400 MHz) δ (ppm): 8.87 (d, J = 8.4 Hz, 1H), 8.63 (d, J = 8.4 Hz, 1H), 8.58 (d, J = 7.2 Hz, 1H), 8.56 (d, J = 7.2 Hz, 1H), 8.46 (t, J = 8.0 Hz and J = 9.2 Hz, 2H), 7.77 (t, J = 8.0 Hz and J = 8.0 Hz, 1H), 7.73 (d, J = 7.6 Hz, 2H), 7.63 (t, J = 7.6 Hz and J = 8.0 Hz, 1H), 7.50 (t, J = 8.0 Hz and J = 7.6 Hz, 2H), 7.36 (d, J = 8.0 Hz, 1H), 7.33 (d, J = 7.6 Hz, 1H), (m, 10H), (m, 2H), (m, 2H), 1.17 (d, J = 6.8 Hz, 12H), 1.07 (d, J = 6.8 Hz, 12H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 29.00, 23.73, MADLI-TF: found: Synthesis of TPMAn: Br Br B(H) 2 B(H) 2 and Suzuki couplings TPMAn Scheme S14 9-(1,2,2-triphenylvinyl)anthracene (TPMAn) A mixture of 1,1-dibromo-2,2-diphenylethene (0.34 g, 1 mmol), phenyl boronic acid (0.12 g, 1 mmol), anthracene boronic acid (0.22 g, 1 mmol), Pd(PPh 3 ) 4 (58 mg, 0.05 mmol), tetrabutyl- ammonium hydrogen sulfate (34 mg, 0.1 mmol), K 2 C 3 (14 mg, 0.1 mmol) in toluene (20 ml) and water (10 ml) was heated to 90 o C and stirred under nitrogen overnight. After cooling down to room temperature, the organic layer was separated and the water layer was extracted with dichloromethane (DCM). The combined organic solution was dried with Na 2 S 4 for several hours. After filtration, the resulting solution was concentrated by rotary evaporator. The residue was purified by column chromatography on silica gel using DCM/PE (v/v: 3:7) as the eluent to obtain the 10-(1,2,2-triphenylvinyl)anthracene (0.13 g, 30.1 %) and DPDAn (84 mg, 31.5 %). 1 HNMR (CDCl 3, 400 MHz) δ (ppm): 8.40 (d, J = 8.4 Hz, 2H), 8.32 (s, 1H), 7.92 (d, J = 8.0 Hz, 2H), 7.34 (m, 6H), 7.25 (m, 3H), 7.08 (m, 2H), 7.01 (m, 3H), 6.89 (d, J = 7.2 Hz, 2H), 6.70 (m, 3H). 13 CNMR (CD 2 Cl 2, 100 MHz) δ (ppm): , , , , , , , , , , , , , , , , , , , , , MADLI-TF: found:
8 2. NMR Spectra. The precursors: N Br ppm N B ppm Figuire S1 and S2 The NMR spectra of the precursors for the synthesis of DPDNI. 8
9 NC Br ppm NC B ppm Figuire S3 and S4 The NMR spectra of the precursors for the synthesis of DPDTPAN. 9
10 Compound ppm ppm Figuire S5 The NMR spectra of (2,2-dibromoethene-1,1-diyl)dibenzene 10
11 Compound DPDT ppm ppm Figuire S6 The NMR spectra of the DPDT 11
12 Compound DPDN ppm ppm Figuire S7 The NMR spectra of the DPDN 1 12
13 Compound DPDN ppm ppm Figuire S8 The NMR spectra of the DPDN 2 13
14 Compound DPDAn ppm ppm Figuire S9 The NMR spectra of the DPDAn 14
15 Compound DPDCz ppm ppm Figuire S10 The NMR spectra of the DPDCz 15
16 Compound DPDTPAN ppm ppm Figuire S11 The NMR spectra of the DPDTPAN 16
17 Compound DPDTPE ppm ppm Figuire S12 The NMR spectra of the DPDTPE 17
18 Compound DPDNI ppm ppm Figuire S13 The NMR spectra of the DPDNI 18
19 Compound TPMAn ppm ppm Figuire S14 The NMR spectra of the TPMAn 19
20 2D-NMR of DPDAn Figure S15 CSY 1 HNMR spectrum of DPDAn 20
21 Figure S16 NESY 1 HNMR spectrum of DPDAn 21
22 Figure S17 HSQC spectrum of DPDAn 22
23 Figure S18 HMBC spectrum of DPDAn Figure S19 1HNMR spectra of DPDAn and TPMAn. 23
24 3. Table S1 Crystallographic data of the DPDN 2, DPDN 1, DPDAn. Structure DPDN 2 DPDN 1 DPDAn DPDAn DPDAn. 0.5CH 2 Cl 2 DPDAn. CH 3 H temperature (K) chemical formula C 34 H 24 C 34 H 24 C 42 H 28 C 42 H 28 C 42 H CH 2 Cl 2 C 42 H. 28 CH 3 H included solvent CH 2 Cl 2 CH 3 H crystal system tetragonal monoclinic Triclinic triclinic triclinic triclinic space group I 4 1 /a P 2 1 /c P -1 P -1 P -1 P -1 formula weight a (Å) (4) (17) (14) (8) (17) (3) b (Å) (4) (12) (17) (9) (18) (3) c (Å) (5) (3) (2) (10) (2) (4) α ( o ) (2) (10) (2) (4) β ( o ) (2) (2) (10) (2) (4) γ ( o ) (2) (10) (2) (4) V (Å 3 ) (15) (6) (4) (19) (4) (7) D c (gcm -3 ) F (000) Z µ (mm -1 ) R 1,[I > 2σ(I)] R 1, (all data) ωr 2, [I > 2σ(I)] ωr 2, (all data) R int GF
25 4. The short contacts in DPDAn 0.5CH 2 Cl 2 crystal. Figure S20 The short contacts in DPDAn. 0.5CH 2 Cl 2 crystal, and the yellow dot lines denote as the π π interactions; the blue dot lines denote as the Cl π interactions; the green dot lines denote as the C-H π interactions. 5. The lengths of relative C-C bonds of DPDN 2, DPDN 1, DPDAn Figure S21 the distance of relative C-C bonds of DPDN 2, DPDN 1, DPDAn from molecular modeling via Gaussian packages. 25
26 6. PL emission spectrum of DPDAn in THF solution (10-5 M). 0.9 DPDAn 10-5 in THF solution Figure S22 PL emission spectrum of DPDAn in THF solution (10-5 M). 7. The absorption spectra of TAE compounds in THF and 99 % water-thf mixture solvents. Figure S23 The absorption spectra of TAE compounds in THF and 99 % water-thf solvent mixture. 26
27 8. The thin film absorption spectra of TAEs Absorption (a.u.) DPDT DPDN 1 DPDN 2 TPMAn DPDAn DPDCz DPDTPAN DPDTPE DPDNI Wavelength (nm) Figure S24 The thin film absorption spectra of TAEs. 9. The CV measurement of DPDCz C-V measurements of DPDCz Current/A Voltage/V Figure S25 The CV measurement of DPDCz 27
28 10. The TGA data of TAE compounds a Weight % DPDT DPDN 1 DPDN 2 TPMAn DPDAn DPDCz DPDTPAN DPDTPE DPDNI Tempreture / o C b Weight % 100 DPDAn DPDAn. 0.5CH2Cl2 DPDAn.CH3H Temperature / C Figure S26 The TGA scans of TAE compounds. 28
29 11. HM and LUM levels of this species from modeling in vacuo. 0 HM LUM Energy / ev NC CN DPDN 2 DPDN 1 DPDT DPDNI DPDTPE DPDTPAN DPDCz DPDAn TPMAn Figure S27 HM and LUM level of this species from modeling in vacuo. 29
30 12. XRD patterns of the as prepared samples: DPDT, DPDCz, DPDTPE, DPDTPAN, DPDNI. DPDT Intensity (a. u.) DPDCz DPDTPE DPDTPAN DPDNI θ / degree Figure S28 XRD patterns of the as prepared samples: DPDT, DPDCz, DPDTPE, DPDTPAN, DPDNI. 13. SEM imaging of DPDTPAN Figure S29 SEM imaging of DPDTPAN 30
31 14. The selected torsion angles in crystals of DPDAn, DPDAn. CH 3 H, DPDAn. 0.5CH 2 Cl 2. Table S2 The selected torsion angles in crystals of DPDAn, DPDAn. CH 3 H, DPDAn. 0.5CH 2 Cl 2. Stucture DPDAn DPDAn 0.5CH 2 Cl 2 DPDAn CH 3 H torsion angle torsion angle torsion angle C30-C29-C15-C C30-C15-C16-C C30-C15-C1-C C30-C29-C1-C C30-C15-C1-C C30-C15-C16-C C29-C30-C31-C C15-C30-C37-C C15-C30-C37-C C29-C30-C37-C C15-C30-C31-C C15-C30-C31-C The dihedral angles of DPDN 2, DPDN 1 and DPDAn in crystal state and molecular modeling in vacuo. Table S3 The dihedral angles of DPDN 2, DPDN 1 and DPDAn in crystal state and molecular modeling in vacuo. Stucture Crystal state Molecular modeling DPDN 2 DPDN 1 DPDAn DPDN 2 DPDN 1 DPDAn dihedral angles of two phenyl rings o o o o o o dihedral angles of two acene rings o o o o o o 31
32 16. The λ abs of the TAEs in 99 % water-thf mixture solvents and thin films Table S4 The λ abs of the TAEs in 99 % water-thf mixture solvents and thin films. λ a abs (abs)/ nm THF Solution a Water-THF Solution a film T d DPDT DPDN DPDN DPDAn TPMAn DPDCz DPDTPAN DPDTPE DPDNI The Comparisons of energy level of TAEs obtained from and the onset wavelength (λ onset ) of the absorption spectra molecular modeling in vacuo and PCM model with THF as the solvent. Table S5 The Comparisons of energy level of TAEs obtained from and the onset wavelength (λ onset ) of the absorption spectra molecular modeling in vacuo and PCM model with THF as the solvent HM a LUM a a E g HM b LUM b b E g HM c LUM d e E g DPDT DPDN DPDN DPDAn TPMAn DPDCz DPDTPAN DPDTPE DPDNI a HM and LUM levels of TAEs obtained from molecular modeling in vacuo, and b HM and LUM levels of TAEs obtained from molecular modeling using PCM model with THF as the solvent simulated based on Gaussian program; c HM (highest occupied molecular orbital) = -(E onset-ox E ferrocene ), where E ferrocene = V, estimated using cyclic voltammetry using Bu4NPF6 in dry DCM; d LUM (lowest unoccupied molecular orbital) = (E g +HM); e E g = optical band gap estimated from the onset wavelength (λ onset ) of the absorption spectra. 32
33 18. The HM, LUM levels from molecular modeling Table S6 The HM, LUM levels from molecular modeling LUM a HM a LUM b HM b a HM and LUM levels of TAEs obtained from molecular modeling using gas phase, and b HM and LUM levels of TAEs obtained from molecular modeling using PCM model with THF as the solvent. 33
34 19. REFERENCES. 1. Gong W.-L., Zhong F., Aldred M. P., Fu Q., Chen T., Huang D.-K., Shen Y., Qiao X., Ma D., Zhu M.-Q., RSC Adv 2012, 2, Huang J., Su J.-H., Li X., Lam M.-K., Fung K.-M., Fan H.-H., Cheah K.-W., Chen C. H., Tian H., J. Mater. Chem. 2011, 21, (a) Aldred M. P., Li C., Zhang G.-F., Gong W.-L., Li A. D. Q., Dai Y., Ma D., Zhu M.-Q., J. Mater. Chem. 2012, 12, (b) Zhang G.-F., Aldred M. P., Gong W.-L., Li C., Zhu M.-Q., Chem. Comm. 2012, 48, Weil T., Reuther E., Beer C., Müllen K. Chem. Eur. J. 2004, 10, (a) Wang S., Bazan G. C., J. Am. Chem. Soc. 2000, 122, (b) Yuan W. Z., Gong Y., Chen S., Shen X. Y., Lam J. W. Y., Lu P., Lu Y., Wang Z., Hu R., Xie N., Kwok H. S., Zhang Y., Sun J., Tang B. Z., Chem. Mater. 2012, 24, Donovan P. M.; Scott L. T., J. Am. Chem. Soc. 2004, 126,
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