Novel Catalytic Oxidative Synthesis of Soluble Conductive Polymers of Poly(3-butoxycarbonyl-4-methylpyrrole)

Abstract

A soluble conductive polymer, poly(3-butoxycarbonyl-4-methylpyrrole) was synthesized by catalytic oxidative polymerization of 3-butoxycarbonyl-4-methylpyrrole, where only a small amount of iron (III) chloride as a catalyst, and enough amount of oxygen as an oxidant were used. Addtion of BF3·Et2O to the reaction system can make the yield of the polymer remarkably increase.

Iron(iii) chloride in oxidative C–C coupling reactions

“…Also 3-aryl-substituted thiophene derivatives (120 with R = aryl) 78 and related compounds including bi-and terthiophenes with octyl substituents 95 have been polymerised with FeCl 3 as oxidant and their properties were investigated.…”

“…In this context, for example, Ohno and Toshima carried out catalytic polymerisations of 3-butoxycarbonyl-4-methylpyrrole (108) to give the corresponding polymeric product as a soluble conducting polymer 109 (Scheme 25). 78 As catalyst 20 mol% of FeCl 3 were applied (at ambient temperature for 24 h), and in a solution of CHCl 3 and butyl acetate oxygen was used for the recycling of the intermediately reduced iron(II) species. Arsalani and Geckeler followed an alternative strategy, and they prepared a polypyrrole hybrid material 110 starting from poly(ethylenimine) and pyrrole.…”

Recent Uses of Iron (III) Chloride in Organic Synthesis

“…In the particular case of ferric chloride, Sato and co-workers have described the oligomerisation of a variety of aromatic tertiary amines 1 by chemical oxidative coupling using FeCl 3 (Scheme 1) [8]. Ohno and Toshima have employed iron (III) chloride as an efficient catalyst in the polymerisation of 3butoxycarbonyl-4-methylpyrrole (BMP) (3), leading to a soluble conductive polymer 4 in THF and NMP (Scheme 2) [10]. The same group also reported the related formation of a linear poly(4methyltriphenylamine) at 50 ºC in the presence of 4 mol equivalent of FeCl 3 under nitrogen atmosphere in chloroform or propylene carbonate [9].…”