Polymethylene pyrroles and electrically conductive polymers ther

Chemistry: electrical and wave energy – Processes and products

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528423, C25B 100

Patent

active

044876670

ABSTRACT:
Cycloalk-2-enes and cycloalk-2-ene-dienes are found to be Michael acceptors which react with tosylmethylisocyanide to form bicyclo fused-ring compounds. A wide variety of substituents may be introduced on the alkylene ring with the aid of the carbonyl group(s) on the fused-ring compound.
These carbonyl-containing bicyclo fused-ring compounds may be reduced to provide monomers which may be electrodeposited as substituted polypyrroles ("PP") which are electrically conductive, compactable and extrudable organic polymers. By choice of substituents on the alkylene ring which bridges the 3- and 4- carbon atoms of the pyrrole ring, the PP may be tailored for use either as a semiconductor having a conductivity in the range from about 10.sup.-5 to about 10.sup.-2 S/cm, or a relatively good conductor having a conductivity in the range from about 10.sup.-2 to about 10.sup.2 S/cm.
A method is disclosed for preparing a polymethylene-substituted pyrrole comprising reacting a cyclic mono- or di-ketone Michael acceptor selected from the group consisting of cycloalk-2-enes and cycloalk-2-dienes, with tosylmethylisocyanide, in the presence of a solvent, so as to form an azabicycloalkylene(di)one, directly, without substituting the N-adjacent carbon atoms on the pyrrole ring.

REFERENCES:
patent: 3574072 (1971-04-01), Louvar
patent: 3828008 (1974-08-01), Shinohara
patent: 3862094 (1975-01-01), Shinohara
patent: 4401545 (1983-08-01), Naarmann
Chem. Society, London Journ. Chem. Comm., 1979, 14 635 and 15 854.

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