Synthesis and characterization of all-conjugated diblock copolymers consisting of thiophenes with a hydrophobic alkyl and a hydrophilic alkoxy side chain

Abstract

Novel thiophene-based all-conjugated block copolymers consisting of 3-hexylthiophene and 3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}thiophene were synthesized using the Grignard metathesis (GRIM) polymerization method in the presence of Ni(dppp)Cl-2. Favorable transfer of the catalytic site from an electron-poor precursor to an electron-rich monomer was found to produce the block copolymer. The molecular weights of the copolymers increased slightly with increasing polymerization temperature (10.1 x 10(3) M-n (35 degrees C) -> 11.1 x 10(3) M-n (55 degrees C)), suggesting that transit of the catalytic site was accelerated at high temperatures. Size exclusion chromatography, UV-vis and photoluminescence spectroscopies, and cyclic voltammetry measurements confirmed that the polymers were block copolymers. The blocks were associated and organized relative to one another in adjacent chains. (C) 2011 Elsevier Ltd. All rights reserved.