Design and Synthesis of a Low Band Gap Conjugated Macroinitiator: Toward Rod−Coil Donor−Acceptor Block Copolymers

A new strategy for the synthesis of a soluble and well-defined dioctylpoly(thienylenevinylene) (DO-PTV), a low band-gap semiconducting polymer, via Horner−Wadsworth−Emmons condensation is presented. The chain length of the DO-PTV can be tuned by varying the amount of end-capping agent employed. This polymer was characterized by 1 H NMR, UV−vis absorbance spectroscopy, and GPC. Finally, the DO-PTV was transformed into macroinitiator for nitroxide mediated radical polymerization. A preliminary experiment of polymerization of a mixture of styrene and chloromethylstyrene with this macroinitiator led to a low band gap rod−coil conjugated block copolymer which is a precursor for a donor−acceptor self-organized material.