Synthesis and structure-property studies of thiophene-benzene alternating copolymers

CHED 689

Megan A. Lang, langma1@gcc.edu, Department of Chemistry, Grove City College, GCC #470, 200 Campus Drive, Grove City, PA 16127 and Mark D. Watson, mdwatson@uky.edu, University of Kentucky, Department of Chemistry, 316 Chemistry Physics Building, Lexington, KY 40506-0055.
We report preliminary studies to elucidate the effect of side-chain identity on the properties of conjugated copolymers with backbones consisting of alternating 3,3'-dialkyl bithiophenes (head-to-head) and 2,5-dialkoxybenzenes. While similar polymers have been reported, we report here the beginning of a systematic study of the role of side chains. Specific properties investigated are the optoelectronic properties and self-assembly in the solid state, which are dictated by the degree of torsion along the polymer backbone. The synthesis of three monomers, and two polymers are described. Two polymers were studied having side chains of n-C12H25 and 2-ethyl hexyl. Results from optical absorption and emission measurements, differential scanning calorimetry (DSC), variable temperature polarized optical microscopy (VT-POM) and wide angle X-ray diffraction (WAXD) indicate significant torsion along the polymer backbones both in solution and solid state, and no propensity towards p-stacking. This is in contrast to similar polymers with bithiophene units carrying alkoxy side chains published by others.