E. Smela et al., THIOL-MODIFIED PYRROLE MONOMERS - 1 - SYNTHESIS, CHARACTERIZATION, AND POLYMERIZATION OF 1-(2-THIOETHYL) PYRROLE AND 3-(2-THIOETHYL)PYRROLE, Langmuir, 14(11), 1998, pp. 2970-2975
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.