Study of Cross-Coupling Reactions for Precisely Controlled Synthesis of π-Conjugated Polymers

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All-cis poly (arylene vinylene) s (PAVs) with the vinylene linkages entirely controlled to cis geometry possess an excellent film-forming property, and undergo photo-induced insolubilization along with cis-to-trans isomerization in thin films, giving all-trans PAVs with good charge-carrier mobility up to 3.5×10^<-2> cm^2 V^<-1> s^<-1>. Highly selective ways of synthesizing all-cis and all-trans PAVs have been developed based on detailed mechanistic studies of elementary processes of palladium-catalyzed cross-coupling reactions. The primary structures of polymers that are required for the photo-induced insolubilization of PAVs have been elucidated by a quantitative method. A novel catalytic system that converts 2-bromo-3-alkylthiophenes to highly head-to-tail regioregular poly (3-alkylthiophene) s (HT-P3ATs) has been developed.