THIOL-MODIFIED PYRROLE MONOMERS - 1 - SYNTHESIS, CHARACTERIZATION, AND POLYMERIZATION OF 1-(2-THIOETHYL) PYRROLE AND 3-(2-THIOETHYL)PYRROLE

To try to solve the problem of delamination of polypyrrole from gold d uring electrochemical cycling, 1-(2-thioethyl)pyrrole and 3-(2-thioeth yl)pyrrole were synthesized as adhesion promoters. These compounds wer e designed to bind to gold through the sulfur atom to form monolayers, and their alkyl chains were made short to permit electron transfer to and from the pyrrole moieties. It was hoped that during electropolyme rization of unmodified pyrrole in solution, the pyrrole moieties of th e monolayer would be incorporated into the growing film. In this first paper of the series, the synthesis and characterization of the monome rs and their electrochemical polymerization to form thin films is pres ented. Nuclear magnetic resonance and infrared, Raman, US-vis-NIR, and mass spectroscopy measurements form a basis for comparison with monol ayers adsorbed on gold surfaces in the following papers.