Synthesis of 1-amino-2,5-di(2-thienyl)benzenes as potential monomers for the preparation of hybrid polythiophene anionic sensors

Abstract

A convenient method for the synthesis of 1-amino-2,5-di(2-thienyl)benzenes was proposed. The method involves in situ generation of aryne intermediates from 1-halo-2,5-di-(2-thienyl)benzenes in the presence of strong bases followed by reactions of the arynes with polyfunctional primary and secondary amines. The products obtained in 75-85% yields are promising monomers for the preparation of polythiophene anionic sensors. Polymerization of dibrominated 1-piperidino-2,5-di(2-thienyl)benzene gave the corresponding poly[(bithiophenediyl)(phenylene)]. © 2012 Springer Science+Business Media New York.