Synthesis and electropolymerization of a series of 2,2′-(ortho-carboranyl)bisthiophenes

A series of 5,5'-functionalized 2,2'-(ortho-carboranyl)bisthiophene with bromo, vinyl, trimethylsilylethyne, N-methylpyrrole or thienyl groups was synthesized and all compounds were characterized by NMR, MS, and X-ray analysis. Electrochemical characterizations of 12a,b and 13a,b were conducted, and the di(thienyl-N-methylpyrrole)-o-carborane 12a and di(bisthieny1)-o-carborane 12b were successfully electropolymerized on a suitable anode to produce the corresponding conducting polymers. OFT calculations are consistent with the electrochemical data. (C) 2016 Elsevier B.V. All rights reserved.