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1 Supporting Information Solid-state Conversion of Processable 3,4-Ethylenedioxythiophene (EDOT) Containing Poly(arylsilane) Precursors to π-conjugated Conducting Polymers Jayesh G. Bokria, Arvind Kumar, Venkataramanan Seshadri, Arlene Tran, Gregory A. Sotzing* Department of Chemistry and the Polymer Program, Institute of Materials Science, University of Connecticut, Storrs, Connecticut , USA Chemicals. 3,6- dibromocarbazole, anhydrous DMF, dry sodium hydride, magnesium bromide etherate (MgBr 2.2Et 2 O), [bis(diphenylphosphino)propane]-nickel(ii) chloride, CDCl 3 and tetrabutylammonium hexafluorophosphate (TBAPF 6 ) were used as received from Aldrich. 3,4-ethylenedioxythiophene (EDOT) was purchased from Aldrich and distilled under vacuum before use. Tetrahydrofuran (THF) was dried over potassium/ benzophenone ketyl, and acetonitrile (ACN) was dried over calcium hydride under nitrogen atmosphere prior to use. n-buli (2.5 M in hexanes) was purchased from Aldrich, and titrated against sec-butanol using 1,10-phenanthroline as indicator under nitrogen atmosphere. Dimethyldichlorosilane and dioctyldichlororsilane were purchased from Gelest, and distilled under nitrogen atmosphere. n-pentane was purchased from ACROS and used as received. 2,2 -bis-(3,4-ethylenedioxy)thiophene (BEDOT) was
2 prepared as per the procedure reported earlier. 1 3,6-bis(3,4-ethylenedioxythiophene)-9- methyl-9h-carbazole (BEDOT-NMCz) was prepared according to the reported procedure. 2 7 X 50 X 0.7 mm ITO-glass (unpolished float glass) with Rs = 5-15 Ω was purchased from Delta Technologies Inc. Insrumentation. 1 H-NMR and 13 C-NMR data were collected on either a Brüker 400 or 500 FT-NMR spectrometer. Chemical shifts are reported as δ ppm downfield from TMS, and residual solvent peak was used as the reference. Peak multiplicities are reported as: b = broad signal, s = singlet, d = doublet, t = triplet, and m = multiplet. Polymers 1 were drop-cast onto KBr pellets to acquire FTIR data using a Niclotet Magna 560 FTIR spectrometer. Waters 150-C plus Gel Permeation chromatograph (GPC) was used to determine molecular weight of 1 using monodisperse poly(styrene) standards. TA Instruments DSC 2920 and Hi-Res TGA 2950 were used to determine thermal properties of 1. A CH Instruments, CHI-400 potentiostat was used for all electrochemical experiments. Electrochemical quartz crystal microbalance (EQCM) experiments were performed on polished quartz crystals having diameter Au key-electrodes on either sides with a resonant frequency of MHz (International Crystal Manufacturing) were used. Optical data were obtained using Perkin Elmer Lambda 900 spectrophotometer equipped with win-lab software. A Philips ESEM 2020 equipped with an EDAX CDU/SUTW thin window environmental scanning electron microscope was used for energy dispersive X-ray (EDX) analysis. Synthesis of 1. General procedure involved taking EDOT, BEDOT or BEDOT- NMCz (x mol) in a vacuum-dried three-neck 250 ml round bottom flask followed by cannulating freshly distilled anhydrous THF. n-buli (2x mol) was added dropwise into
3 the reaction mixture at -78 C, and stirred for 1hour. The reaction mixture was stirred for another one hour at room temperature, and then cooled to 0 C before adding dialkyldichlorosilane (1x mol) drop-wise over a period of minutes. The reaction was quenched after stirring at room temperature for 48 hours under nitrogen atmosphere using water. Polymer obtained was precipitated using n-pentane, and dried under vacuum. Purification was done by washing 1a with pentane, and 1b and 1c with pentane THF (50:50) mixture. Purified yield for 1a, 1b and 1c were found to be 63, 56 and 67 %, respectively. Characterization of 1a. 1 H-NMR (CDCl 3 ): δ (ppm) = 4.11 (4H, b); 0.57 (6H, b). 13 C-NMR (CDCl 3 ): δ (ppm) = 148.4, 142.5, 115.4, 105.8, 64.4, 34.2, 22.4, 14.1, FTIR (cm -1 ) = 2966, 1648, 1422, 1347, 1248, 1168, 1089, 1053, 974, 840. Electronic spectrum (film): λ max = 256 nm. Number-average molecular weight, M n =50,600 with a polydispersity of Glass transition temperature, T g = 68 C, and onset of thermal degradation = 290 C. Characterization of 1b. 1 H-NMR (DMSO): δ (ppm) = 4.27 (4H, b); 4.20 (4H, b); 0.51 (6H, b). FTIR (cm -1 ) = 2955, 1469, 1437, 1362, 1260, 1171, 1091, 1061, 966, 800. Electronic spectrum (film): λ max = 347 and 375 nm. Glass transition temperature was not observed up to its onset of thermal degradation = 200 C. No GPC data was available due to the insolubility in common GPC solvents. Characterization of 1c. 1 H-NMR (CDCl 3 ): δ (ppm) = 8.44 (2H, b); 7.87 (2H, b); 7.39(2H, b); 4.31 (4H, b); (3H, b); 1.29 (23H, b); (11H, b). 13C- NMR (CDCl3): δ (ppm) = 140.1, 137.2, 124.7, 122.8, 118.4, 113.3, 108.6, 99.7, 64.5, 33.6, 32.0, 29.3, 23.7, 22.7, FTIR (cm -1 ) = 3103, 3072, 2942, 2860, 1454, 1431,
4 1384, 1365, 1241, 1175, 1093, 969, 842, 830, 700. Electronic spectrum (film): λ max = 253 and 315 nm. Number-average molecular weight, M n =85,200 with a polydispersity of Glass transition temperature, T g = 35 C, and onset of thermal degradation = 250 C. Electrochemistry. A three electrode cell containing platinum button as working, platinum flag as counter, and Ag/ Ag + non-aqueous as a reference electrode was used in the presence of monomer free 0.1 M TBAPF 6 / ACN electrolyte solution for all solidstate studies. Reference electrode was calibrated using ferrocene-ferrocenium redox, and found to be vs. NHE. 1 was drop cast onto the Pt button, and kept in electrolyte for between 1 to 10 minutes prior to the electrochemical polymerization. Electrochemical polymerization was performed by using cyclovoltammetry at a scan rate of 50 mv/s. Redox behavior of the resulting polymer, 2, was performed using fresh electrolyte solution at a scan rate of 50 mv/s. Solution electrochemical studies were performed using a 3.8 mm solution of 1a in 0.1 M TBAPF 6 /CH 2 Cl 2. The electrochemically generated polymer poly(1a) was deposited on a Pt button working electrode, using a Pt-flag counter and a non-aqueous Ag/Ag + reference, and cyclovoltammogram is shown in figure 1. After the electrochemical deposition of the polymer, the working electrode was washed with ACN, and polymer CV acquired using a fresh 0.1 M TBAPF 6 / CH 2 Cl 2 (Figure 2).
5 Figure 1. Solution electropolymerization of 1a using 3.8 mm solution of 1a in 0.1 M TBAPF 6 / CH 2 Cl 2 at a scan rate of 50 mv/s. Potential reported vs Ag/ Ag+ non-aqueous reference electrode (0.457 Vs NHE) Figure 2. Cyclovoltammogram of poly(1a) in a 0.1 M TBAPF 6 / CH 2 Cl 2 at a scan rate of 50 mv/s. Potential reported vs Ag/ Ag+ non-aqueous reference electrode (0.457 Vs NHE) Insitu Spectroelectrochemistry. Polymer 1a or 1c solution in chloroform or DMF was spin coated onto ITO-coated glass which was used as working electrode in the
6 presence of 0.1 M TBAPF 6 / ACN. Another ITO-coated glass used as counter electrode was kept at 0.5 cm apart from the working electrode, and Ag/ Ag + reference electrode was kept in between them inside a quartz cuvette. The spectra of the polymer in its different oxidized states were obtained by applying constant potentials as reported in Figure 2 in the article. References 1. G. A.Sotzing, J. R. Reynolds Adv. Mater 1997, 9, G. A.Sotzing, J. L. Reddinger, A. R. Katritzky, J. Soloducho, R. Musgrave, J. R. Reynolds, P. J. Steel Chem. Mater. 1997, 9, 1578.
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