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(bisthienyl)- o -carborane 12b were successfully electropolymerized on a suitable anode to produce the corresponding conducting polymers. DFT calculations are consistent with the electrochemical data. [ABSTRACT FROM AUTHOR]