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 H-1 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.