Naphthobipyrrole: Versatile Synthesis and Electropolymerization

Naphthobipyrrole: Versatile Synthesis and Electropolymerization

A facile synthetic route to a new polycyclic pyrrole derivative, 3,8-diethyl-1,10-dihydro-benzo[e]pyrrolo[3,2-g]indole (1), is reported. This annulated bipyrrole acts as a monomer for electropolymerization and forms an electrochromic conducting polymer (poly1) when electrooxidized at low potentials...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 75; no. 24; pp. 8355 - 8362
Main Authors: Roznyatovskiy, Vladimir V, Roznyatovskaya, Nataliya V, Weyrauch, Hubert, Pinkwart, Karsten, Tübke, Jens, Sessler, Jonathan L
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 17-12-2010
Subjects:
Chemistry
Electrochemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Miscellaneous (electroosmosis, electrophoresis, electrochromism, electrocrystallization, ...)
Organic chemistry
Preparations and properties
Conducting polymers
Annelation
Scanning electron microscopy
Regioselectivity
Nitrogen heterocycle
Acetonitrile
Silver compound
Polycyclic compound
Electrochromism
Chemical synthesis
Silver I
Pyrrole derivatives
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Summary:A facile synthetic route to a new polycyclic pyrrole derivative, 3,8-diethyl-1,10-dihydro-benzo[e]pyrrolo[3,2-g]indole (1), is reported. This annulated bipyrrole acts as a monomer for electropolymerization and forms an electrochromic conducting polymer (poly1) when electrooxidized at low potentials (0.4 V vs Ag/Ag+) in acetonitrile. The presence of alkyl substituents at the 3 and 8 carbons (β-pyrrolic positions) induces regioselective 2,5′-coupling of the pyrrole repeat units and gives rise to the more uniform polymeric product, poly1. Poly1 exhibits globular morphology, as judged from SEM pictures. Its spectroelectrochemical features can be attributed to the formation of four possible states: neutral, polaron, bipolaron, and transverse bipolaron. The relatively low switching potentials (−0.6 to +0.9 V vs Ag/Ag+ in MeCN) displayed by poly1 leads us to suggest that 1 has a role to play as a polymerizable moiety for the development of multicolor electrochromic materials.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo1016426