1,4-Benzene-Bridged Covalent Hybrid of Triarylamine and Cyclometalated Ruthenium: A New Type of Organic-Inorganic Mixed-Valent System
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1 Supporting Information for: 1,4-Benzene-Bridged Covalent Hybrid of Triarylamine and Cyclometalated Ruthenium: A ew Type of Organic-Inorganic Mixed-Valent System Chang-Jiang Yao, Ren-Hui Zheng, Qiang Shi, Yu-Wu Zhong,*,, and Jiannian Yao Beijing ational Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing , P. R. China. State Key Laboratory of Coordination Chemistry, anjing University, anjing , People s Republic of China *Correspondance: Prof. Yu-Wu Zhong CAS Key laboratory of photochemistry Institute of Chemistry, Chinese Academy of Sciences Beijing , China zhongyuwu@iccas.ac.cn Website:
2 1. Synthetic Procedures and Characterization General. MR spectra were recorded in the designated solvent on Bruker Avance 400 MHz spectrometer. Spectra are reported in ppm values from residual protons of deuterated solvent for 1 H MR (δ 7.26 ppm for CDCl 3 and 1.92 ppm for CD 3 C) and 13 C MR (δ ppm for CDCl 3 ). MS data were obtained with a Bruker Daltonics Inc. ApexII FT-ICR or Autoflex III MALDI-TOF mass spectrometer. The matrix for MALDI-TOF measurement is -cyano-4-hydroxycinnamic acid. Microanalysis was carried out using Flash EA 1112 or Carlo Erba 1106 analyzer at the Institute of Chemistry, Chinese Academy of Sciences. Br Br Br PdCl 2 (PPh 3 ) 2, LiCl + SnBu 3 PhCH 3, 24h Br To a solution of 1,3,5-tribromobenzene (1.0 mmol, 320 mg) and 2-(tributylstannyl)pyridine (2.2 mmol, 810 mg) in 20 ml dry toluene were added PdCl 2 (PPh 3 ) 2 (0.2 mmol, 140 mg) and LiCl (10 mmol, 424 mg) under a 2 atmosphere. The mixture was bubbled with nitrogen for 10 min before the vial was capped and heated at C for 48 h. After the reaction was cooled to room temperature, the solvent was removed under reduced pressure. The residue was then subjected to column chromatography on silica gel (eluent: CH 2 Cl 2 /ethyl acetate/h 4 OH 100/10/0.05) to afford 106 mg 3,5-di(2-pyridyl)bromobenzene as a yellow solid in a yield of 34%. 1 H MR (400 MHz, CDCl 3 ): δ 7.28 (m, 2H), 7.80 (m, 4H), 8.21 (s, 2H), 8.54 (s,1h), 8.70 (d, J = 4.6 Hz, 2 H). Br OMe MeO OMe + H Pd 2 (dba) 2, dppf PhCH 3, ao t Bu OMe To a solution of 3,5-di(2-pyridyl)bromobenzene (1.0 mmol, 323 mg) and 4,4'-dimethoxydiphenylamine (1.5 mmol, 344 mg) in 20 ml dry toluene were added Pd 2 (dba) 3 (0.02 mmol, 18.3 mg), 1,1'-bis(diphenylphosphino)ferrocene (dppf) (0.02 mmol, 11.1 mg) and ao t Bu (1.2 mmol, mg) under a 2 atmosphere. The mixture was bubbled with nitrogen for 10 min before the vial was capped and heated at C
3 for 48 h. After the reaction was cooled to room temperature, the solvent was removed under reduced pressure. The residue was then subjected to column chromatography on silica gel (eluent: CH 2 Cl 2 /ethyl acetate/h 4 OH 75/6/1) to afford 317 mg 1-di-p-anisylamino-3,5-di(2-pyridyl)benzene as a yellow solid in a yield of 69%. 1 H MR (400 MHz, CDCl 3 ): δ 3.78 (s, 6 H), 6.82 (d, J = 8.3Hz, 4 H), 7.10 (d, J = 8.3 Hz, 4 H), 7.18 (t, J = 5.3 Hz, 2 H), 7.65 (s, 2 H), 7.67 (d, J = 5.3 Hz, 4 H), 8.12 (s, 1 H), 8.63 (d, J = 4.3 Hz, 2 H). 13 C MR (100 MHz, CDCl 3 ): δ 55.4, 114.7, 118.4, 120.3, 120.8, 122.1, 126.3, 126.4, 136.6, 140.8, 141.1, 149.4, 155.6, EI-MS (m/z): 537 [M + 2K] +. MeO (PF 6 ) 2 OMe + Cl 3 Ru DMF/tBUOH microwave KPF 6 Ru MeO 1 2+ OMe To a mixture of 3 ml DMF and 3 ml t-buoh were added 1-di-p-anisylamino-3,5-di(2-pyridyl)benzene (0.1 mmol, 46 mg) and Ru(tpy)Cl 3 (0.1 mmol, 44 mg). The mixture was heated under microwave conditions for 50 min at a power of 200 W and then another 30 min at a power of 375 W. After cooling down to room temperature, an excess of aqueous KPF 6 were added. The resulting precipitate was collected by filtration and wash successively with water and ether. The crude product was purified by column chromatography on silica using acetonitrile/water/saturated aq. KO 3 30/1/0.05 as the eluent to give 56 mg [1](PF 6 ) 2 as a black solid (yield: 52%). MALDI-MS (m/z): for [M-2PF 6 ] 2+. Anal. Calcd for: C 45 H 35 F 12 6 O 2 P 2 Ru. 2H 2 O: C, 48.31; H, 3.51;, Found: C, 48.64; H, 3.28;, OMe (PF 6 ) OMe Cl 3 Ru + HOCH 2 CH 2 OH microwave Ru OMe 2 + OMe To 5 ml ethylene glycol were added [(2,3-di(2-pyridyl)-4-di-
4 p-anisylaminopyridine)rucl 3 ] 1 (0.05 mmol, 33.4 mg), 1,3-di(2-pyridyl)benzene (0.05 mmol, 11.6 mg). The mixture was heated under microwave conditions (power = 375 W) for 30 min. After cooling down to room temperature, an excess of aqueous KPF 6 were added. The resulting precipitate was collected by filtration and washing successively with water and ether. The crude product was purified by column chromatography on silica using acetonitrile/water/saturated KO 3 30/1/0.05 as the eluent to give 16 mg [2](PF 6 ) as a black solid (34% yield). 1 H MR (400 MHz, CD 3 C): δ 3.87 (s, 6 H), 6.74 (t, J = 6.6Hz, 2 H), 6.81 (t, J = 6.6 Hz, 2 H), 6.94 (d, J = 5.5 Hz, 2 H), 7.11 (d, J = 8.6 Hz, 4 H), 7.27 (d, J = 5.5 Hz, 2 H), (m, 6 H), 7.61 (t, J = 7.8 Hz, 2 H), 7.96 (s, 2 H), 7.99 (d, J = 8.0 Hz, 2 H), 8.12 (d, J = 8.0 Hz, 2 H), 8.20 (d, J = 7.5 Hz, 2 H). MALDI-MS (m/z): for [M-PF 6 ] +. Anal. Calcd. for C 45 H 35 F 6 6 O 2 PRu. H 2 O: C, 56.54; H, 3.90;, Found: C, 56.05; H, 3.76;, H MR spectrum of [2](PF 6 ): PPM PPM (1) Yao, C.-J.; Yao, J.; Zhong, Y.-W. Inorg. Chem. 2011, 50, 6847.
5 2. Computational Method DFT and TDDFT calculations are carried out using the B3LYP exchange correlation functional 2 and implemented in the Gaussian 03 program package. 3 The electronic structures of complexes were determined using a general basis set with the Los Alamos effective core potential LanL2DZ basis set for ruthenium, and 6-31G* for other atoms in vacuum. 4 All orbitals have been computed at an isovalue of The initial structures for 1 + and 2 + were generated on the basis of a known single-crystal structure of the following complex 1 by removing one di-p-anisylamino segment and replacing one nitrogen atom with a carbon atom. The calculated lengths of the Ru-C bond for 1 + and 2 + are and Å, respectively. Other Ru- lengths are in the range of Å. This is quite reasonable compared to known single-crystal structures of know cyclometalated ruthenium complexes. 5 MeO OMe 2+ Ru MeO OMe (2) (a) Becke, A. D. J. Chem. Phys. 1993, 98, (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. (3) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, Jr. T.; Kudin, K..; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega,.; Petersson, G. A.; akatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; akajima, T.; Honda, Y.; Kitao, O.; akai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; anayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision E.01; Gaussian Inc.: Pittsburgh PA, (4) (a) Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., Ed.; Plenum: ew York, 1976; Vol. 3, p 1. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270. (c) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284. (d) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299. (5) (a) Yang, W.-W.; Zhong, Y.-W.; Yoshikawa, S.; Shao, J.-Y.; Masaoka, S.; Sakai, K.; Yao, J.; Haga, M.-a. Inorg. Chem. 2012, 51, 890. (b) Wadman, S. H.; Havenith, R. W. A.; Hartl, F.; Lutz, M.; Spek, A. L.; van Klink G. P. M.; van Koten, G. Inorg. Chem. 2009, 48, 5685.
6 195 (LUMO+5) 192 (LUMO+2) 191 (LUMO+1) 190 (LUMO) 189 (HOMO) 188 (HOMO-1) 187 (HOMO-2) 186 (HOMO-3) 185 (HOMO-4) Figure S1. Isodensity plots of selected frontier orbitals for LUMO+5 LUMO+2 Eigenvalue/eV LUMO HOMO HOMO-1-8 HOMO Figure S2. Energy level allignment for 1 +.
7 189B 188B 187B Figure S3. Isodensity plots of selected frontier orbitals for B 188B 187B 182B Figure S4. Isodensity plots of selected frontier orbitals for (LUMO+2) 191 (LUMO+1) 190 (LUMO) 189 (HOMO) 188 (HOMO-1) 187 (HOMO-2) 186 (HOMO-3) Figure S5. Isodensity plots of selected frontier orbitals for 2 +.
8 Eigenvalue/eV LUMO+2 LUMO -7-8 HOMO HOMO HOMO-1 HOMO-2 Figure S6. Energy level allignment for B 188B Figure S7. Isodensity plots of selected frontier orbitals for B 187B 185B Figure S8. Isodensity plots of selected frontier orbitals for 2 3+.
9 Table S1. Calculated main low-energy excitations of complexes studied. a compoumd S n E/eV E/nm f dominant transitions (configuration coefficient) (HOMO) 192 (LUMO+2) (0.703) (HOMO) 195 (LUMO+5) (0.68) (HOMO-3) 191 (LUMO+1) (0.657); 185 (HOMO-4) 190 (LUMO) (0.209) (HOMO-4) 191 (LUMO+1) (0.4192); 186 (HOMO-3) 190 (LUMO) (0.4555) B 189B (0.81); 188B 189B (-0.55) B 189B (0.58); 188B 189B (0.75) B 189B (0.98) B 188B (0.8964) (HOMO-1) 190 (LUMO) (0.654) (HOMO-1) 191 (LUMO+1) (0.568) (HOMO-2) 191 (LUMO+1) (0.682) (HOMO-2) 190 (LUMO) (0.62) (HOMO) 192 (LUMO+2) (0.67) B 189B (0.91) B 188B (0.9976) B 188B (0.9677) a Calculated on the level of B3LYP/LanL2DZ/6-31G*/vacuum theory.
10 Cartesian coordinates for DFT-optimized structure of 1 + : Charge = 1 multiplicity = 1 C C C C C C C Ru H C C C C H C C C C C C C C C C C H H H C C C C C C C C C C C C H H H H H C
11 C C C C C C H H H H H H H H H H H H C C H H H H H H H O O C C H H H H H H
12 Cartesian coordinates for DFT-optimized structure of 1 2+ : Charge = 2 multiplicity = 2 C C C C C C C Ru H C C C C H C C C C C C C C C C C H H H C C C C C C C C C C C C H H H H H C
13 C C C C C C H H H H H H H H H H H H C C H H H H H H H O O C C H H H H H H
14 Cartesian coordinates for DFT-optimized structure of 1 3+ : Charge =3 multiplicity = 3 C C C C C C C Ru H C C C C H C C C C C C C C C C C H H H C C C C C C C C C C C C H H H H H C
15 C C C C C C H H H H H H H H H H H H C C H H H H H H H O O C C H H H H H H
16 Cartesian coordinates for DFT-optimized structure of 2 + : Charge = 1 multiplicity = 1 C C C C C C Ru H C C C C C H C C C C C C C C C C C H H H C C C C C C C C C C C C H H H H H C
17 C C C C C C H H H H H H H H H H H H C C H H H H H H H O O C C H H H H H H
18 Cartesian coordinates for DFT-optimized structure of 2 2+ : Charge = 2 multiplicity = 2 C C C C C C Ru H C C C C C H C C C C C C C C C C C H H H C C C C C C C C C C C C H H H H H C
19 C C C C C C H H H H H H H H H H H H C C H H H H H H H O O C C H H H H H H
20 Cartesian coordinates for DFT-optimized structure of 2 3+ : Charge = 3 multiplicity = 3 C C C C C C Ru H C C C C C H C C C C C C C C C C C H H H C C C C C C C C C C C C H H H H H C
21 C C C C C C H H H H H H H H H H H H C C H H H H H H H O O C C H H H H H H
22 EPR measurement: The EPR measurement of 1 2+ (as-prepared sample) was performed in a solution in acetonitrile at room temperature on a Bruker ELEXSYS E500-10/12 spectrometer. The spectrometer frequency is Hz.
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