Synthesis and polymerization studies of 3-(+) and (−)-menthyl carboxylate pyrroles

The synthesis of 3-(−)- and 3-(+)-menthyl carboxylate pyrrole was achieved in four high yielding steps, including the triisopropylsilyl (TIPS) protection of the pyrrole nitrogen, bromination of the 3-position, lithium halogen exchange followed by reaction with menthyl chloroformate, and finally de-protection. Chemical polymerization of both the TIPS protected, and non-protected, menthyl carboxylate pyrroles was performed and the resulting polymers exhibited conductivity ranging from 0.6 to 2.3 S/cm. Polymerization of the 3-menthyl-N-TIPS pyrrole on the surface of wool was achieved by using solution and mist polymerization methods.