Abstract
The synthesis of 2,2′-bipyrroles substituted at positions 5,5′ with pyrrolyl, N-methyl-pyrrolyl and thienyl groups and their application in the preparation of conducting polymers is reported herein. The preparation of these monomers consisted of two synthetic steps from a functionalized 2,2′-bipyrrole: Bromination of the corresponding 2,2′-bipyrrole followed by Suzuki or Stille couplings. These monomers display low oxidation potential compared to pyrrole because of the extended length of their conjugation pathway. The resulting monomers can be polymerized through oxidative/electropolymerization. Electrical conductivity and electrochromic properties of the electrodeposited polymeric films were evaluated using 4-point probe measurements and cyclic voltammetry to evaluate their applicability in electronics.
Highlights
Conducting polymers have demonstrated to be one of the most versatile sets of materials since their serendipitous discovery by Shirakawa and co-workers in 1977 [1]
Once the brominated bipyrroles were in hand, preparation of substituted bipyrroles 1 was carried out by either Stille or Suzuki cross-coupling reactions
Extended bipyrrole 1b was prepared by Stille coupling adapting the methodology used to prepare 1c
Summary
Conducting polymers have demonstrated to be one of the most versatile sets of materials since their serendipitous discovery by Shirakawa and co-workers in 1977 [1]. Conducting polymers have been extensively studied as part of energy storage systems [2,3,4], solar cells [5,6,7], electromagnetic interference shielding [8,9,10], or light-emitting diodes [11,12,13] among others. All these new systems within the framework of conventional electronics have allowed the appearance of new electronic devices such as smart windows, new display devices, or long-lasting batteries [14]. The most extensively studied conducting polymers are polyacetylenes (PA), polyaniline (PANI), polypyrrole (PPy), and polythiophenes (PTh)
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