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Chiral BEDOT-based copolymers prepared by chemical and electrochemical polymerization
Y.S. Jeong,H. Goto,S. Iimura,T. Asano,K. Akagi 한국물리학회 2006 Current Applied Physics Vol.6 No.5
Optically active conjugated copolymers, poly[1,4-bis[2-(3,4-ethylenedioxy)thienyl]-2,5-benzoic acid-1-methylheptyl ester] [poly(BEDOT-B(OCT.)], were synthesized by chemical and electrochemical oxidative polymerizations. Poly[BEDOT-B(OCT.)] of both(R) and (S) conguration were synthesized by introducing chiral octyloxycarbonyl group in the side chain. The dibromo com-pounds, (R)-1 and (S)-1, were prepared by Mitsunobu reaction by an esterication of (R) o r (S)-octanol and 2,5-dibromobenzoicacid with an aid of diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) in tetrahydrofuran. The monomers were thenprepared with Stille coupling technique using Pd(PPh3)4Cl2 as a catalyst to produce (R)-1 and (S)-1. The monomer was electropo-lymerized onto platinum button and ITO glass electrodes by repeated scanning from. 1.0 V to +1.0 V versus Ag/Ag+ at 20 mV/s.The polymer was electrochromic and reversibly switching from purple green upon oxidation. The chemical polymerization was alsocarried out in dimethylformamide with a Ni(cod)2 catalyst. Optical absorption and circular dichroism (CD) measurements wereof chiral polymer with helicity, which can disclose a possibility toward chiralelectrochemistry.