Near Infrared Electrochromism in Electropolymerized Films of Biscyclometallated Ruthenium Complex Bridged by 1,2,4,5-Tetra(2-pyridyl)benzene
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1 Supporting Information for: ear Infrared Electrochromism in Electropolymerized Films of Biscyclometallated Ruthenium Complex Bridged by 1,2,4,5-Tetra(2-pyridyl)benzene Chang-Jiang Yao, Yu-Wu Zhong,, * Hai-Jing ie, Héctor D. Abruña, and Jiannian Yao, * Beijing ational Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 119, People s Republic of China; Baker Laboratory, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, ew York Correspondance: Prof. Yu-Wu Zhong CAS Key laboratory of photochemistry Institute of Chemistry, Chinese Academy of Sciences Beijing 119, China zhongyuwu@iccas.ac.cn Website: List of contents: Synthesis of 2[PF 6 ] Page S2-3 Electropolymerization of 2[PF 6 ] Page S4-S7 XPS spectrum of a polymeric film of 2[PF 6 ] 2 on ITO glass Page S8 S1
2 Synthesis of 2[PF 6 ] 2 tpb RuCl 3 AgOTf DMF/tBuOH Cl 3 Ru Ru Ru EtOH, reflux acetone 13 C (PF 6 ) 2 vtpy [2](PF 6 ) 2 To 4 ml of distilled ethanol were added vtpy 1 (1. mmol, 259 mg) and RuCl 3 3H 2 O (1. mmol, 261 mg). The mixture was refluxed for 4 h before cooling down to room temperature. The resulting precipitate was collected after filtration and washed successively with water and ether to afford Ru(vtpy)Cl 3 as a brown solid (46 mg, 87% yield) which was used in next transformation without further purification. To 4 ml of dry acetone were added Ru(vtpy)Cl 3 (.1 mmol, 47 mg) and AgOTf (.3 mmol, 78 mg). The reaction system was refluxed for 5 h before cooling down to room temperature. The mixture was filtered through celite and the filtrate was concentrated to dryness. To the residue were added 1,2,4,5-tetra(pyridin-2-yl)benzene 2 (tpb,.5 mmol, 19.3 mg), 12 ml DMF and 12 ml t-buoh. The mixture was bubbled with nitrogen for 2 min before the vial was capped and heated at 13 C for 48 h. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was dissolved in 2 ml methanol. After adding an excess of KPF 6, the resulting precipitate was collected by filtering and washing with water and Et 2 O. The crude solid was purified by chromatography on silica gel to give 13 mg bisruthenium complex 2[PF 6 ] 2 as a black solid (eluent: CH 3 C/H 2 O/aq.KO 3 1/1/.1 black solid, 19% yield). Distinct 1 H MR spectrum (shown in the following page) could not be fully assigned due to signal broadening caused by contamination of small amount of mixed-valent complex, which contains paramagnetic Ru III species. MALDI-TOF m/z: 125 [M-PF 6 ] +, [M-2PF 6 ] 2+ (The MS spectrum is shown in the following page). Anal. Calcd for C 6 H 42 F 12 1 P 2 Ru. 2 2H 2 O. Et 2 O: C, 51.7; H, 3.75;, Found: C, 5.99; H: 3.48;, ie, H.-J.; Yao, J.; Zhong, Y.-W. J. Org. Chem. 211, 76, Yao, C.-J.; Zhong, Y.-W.; Yao, J. J. Am. Chem. Soc. 211, 133, S2
3 S3
4 Electropolymerization of 2[PF 6 ] 2 All electrochemical experiment were carried out using a CHI62D potentiostat. All measurements were carried out in.1 M of Bu 4 ClO 4 /acetonitrile with a Ag/AgCl reference electrode. The working electrode is a glassy carbon, and a platinum coil is used as the counter electrode. A three-compartment electrochemical cell was used in electropolymerization experiments. The working electrode (ITO glass) was positioned parallel to and opposite the counter electrode. UV/vis/IR spectra were recorded using a PE Lambda 75 UV/vis/IR spectrophotometer E/V vs Ag/AgCl Figure S1. Reductive electropolymerization of 2 2+ (.6 mm in acetonitrile) on a Pt disk electrode (d = 2 mm) by 1 repeated potential scan cycles at 1 mv/s. Surface coverage = mol/cm 2. S4
5 E/V vs Ag/AgCl Figure S2. Reductive electropolymerization of 2 2+ (.6 mm in acetonitrile) on a Pt disk electrode (d = 2 mm) by 2 repeated potential scan cycles at 1 mv/s. Surface coverage = mol/cm E/V vs Ag/AgCl Figure S3. Reductive electropolymerization of 2 2+ (.6 mm in acetonitrile) on a Pt disk electrode (d = 2 mm) by 4 repeated potential scan cycles at 1 mv/s. Surface coverage = mol/cm 2. S5
6 V vs Ag/AgCl Figure S4. Reductive electropolymerization of 2 2+ (.6 mm in acetonitrile) on an ITO glass electrode (2 8 mm 2 ) by 1 repeated potential scan cycles at 1 mv/s. Surface coverage = mol/cm V vs Ag/AgCl Figure S5. Reductive electropolymerization of 2 2+ (.6 mm in acetonitrile) on an ITO glass electrode (2 8 mm 2 by 3 repeated potential scan cycles at 1 mv/s. Surface coverage = mol/cm 2. S6
7 8 I/ A V vs Ag/AgCl Figure S6. Reductive electropolymerization of 22+ (.6 mm in acetonitrile) on an ITO glass electrode (2 8.5 mm2) by 6 repeated potential scan cycles at 1 mv/s. Surface coverage = mol/cm2. 6 I/ A V vs Ag/AgCl Figure S7. Reductive electropolymerization of 22+ (.6 mm in acetonitrile) on an ITO glass electrode (2 7 mm2) by 75 repeated potential scan cycles at 1 mv/s. Surface coverage = mol/cm2. S7
8 XPS spectrum of a polymeric film of 2[PF 6 ] 2 on ITO glass X-ray photoelectron spectroscopy data were obtained with an ESCALab22i-XL electron spectrometer from VG Scientific using 3W AlKα radiation. The base pressure was about mbar. The binding energies were referenced to the C1s line at ev from adventitious carbon. Survey 1.8E+5 C1s+Ru3d 1.7E+5 1.6E+5 1.5E+5 1.4E+5 O1s Counts / s 1.3E+5 1.2E+5 1.1E+5 1.E+5 9.E+4 8.E+4 7.E+4 6.E+4 5.E+4 4.E+4 Ru3p3 1s 3.E+4 2.E+4 Cl2p 1.E+4.E Binding Energy (ev) Figure S8. XPS spectrum of a polymeric film of [2](PF 6 ) 2. S8
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