Synthesis of conducting poly[di-heteroaromatics] from pyrrole, indole, and carbazole, and their mixed hydroxamates, and studies of their metal complexes

Abstract

Compounds 1,1-di-(N-pyrrolyl)methane hydroxamic acid (II), 1,1-di-(N-indolyl)methane hydroxamic acid (IV), 1,1-di-(N-carbazolyl)methane hydroxamic acid (VI), 1-(N-pyrrolyl)-1-(N-carbazolyl)methane hydroxamic acid (VIII), and 1-(N-pyrrolyl)-1-(N-indolyl)-methane hydroxamic acid (X) were synthesized from their N,N-substituted ester group derivatives. They were chemically polymerized in the presence of oxidants such as ammonium persulfate and iron(III) perchlorate for hydroxamic acid and ester groups derivatives, respectively. The conductivity of these polymers was measured by a four-point probe method. The complexes of hydroxamic acid derivatives with certain ions [such as Fe(III), Rh(III), Ir(III), Cr(III), Cu(II), and Ni(II)] were studied. Compounds II, IV, and VI and their ester group derivatives were successfully electropolymerized by a cyclic voltammetry method under the following conditions: 6 × 10−3 M of monomer, 0.1 M lithium perchlorate, 20 mL of acetonitrile, glassy carbon (GC) disk working electrode, and Ag/AgCl reference electrode and platinum wire counter electrode conditions. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 90: 63–71, 2003