Synthesis of Novel Semiconducting Polymers Consisting of p-Phenylene, p-Phenylenevinylene, and Styrylamine Structures: Copolymerization and Dehydrogenation of 1,3-Cyclohexadiene and 4-Diphenylaminostyrene

Abstract

Well-defined semiconducting copolymers consisting of p-phenylene (PP), p-phenylenevinylene (PV), and styrylamine (SA) ternary molecular structures (PP/PV/SA copolymer) were synthesized by living anionic polymerization for the random copolymerization of 1,3-cyclohexadiene (1,3-CHD) and 4-diphenylaminostyrene (4-DAS) and the complete dehydrogenation of the 1,3-CHD/4-DAS copolymer. To obtain PP/PV/SA copolymer, the 1,3-CHD/4-DAS random copolymer, consisting of the 1,4-cyclohexadiene (1,4-CHD) and cyclohexadiene (CHD)-diphenylaminostyrene (DAS) structures as a prerequisite prepolymer, was prepared by the random copolymerization of 1,3-CHD and 4-DAS with tert-butyllithium in cyclohexane. The completely dehydrogenated 1,3-CHD/4-DAS random copolymer was achieved without decomposition of the polymer chain when 2,3,5,6-tetrachloro-1,4-(p-)-benzoquinone was used as a dehydrogenation reagent. Gel permeation chromatography, 1H nuclear magnetic resonance, UV/vis, and photoluminescence analyses confirmed that the compl...