Affordable Access

Publisher Website

Electrosynthesis of 2,7-linked polycarbazole derivatives to realize low-bandgap electroactive polymers

Authors
Journal
Synthetic Metals
0379-6779
Publisher
Elsevier
Publication Date
Volume
160
Identifiers
DOI: 10.1016/j.synthmet.2010.08.023
Keywords
  • Electrochemical Polymerization
  • Electrochromism
  • π-Conjugated Polymer
  • Poly(2
  • 7-Carbazole)
Disciplines
  • Chemistry

Abstract

Abstract Poly(2,7-carbazole) derivatives have been synthesized because they have more extended conjugation lengths and lower energy bandgaps than poly(3,6-carbazole)s; however, few studies regarding electrochemical synthesis of poly(2,7-carbazole)s have been reported. Here, a series of N-alkylated-2,7-di(2-furyl)carbazoles, N-butyl-2,7-di(2-thienyl)carbazole, and N-butyl-2,7-di(2-(3,4-ethylenedioxthienyl))carbazole, were synthesized to obtain electroactive films of poly(2,7-carbazole) derivatives by electrochemical polymerization. Cyclic voltammetry revealed that these monomers have excellent polymerization activity, due to their low oxidation potentials (<0.57 V vs. ferrocene (Fc/Fc +)), and the corresponding polymers exhibit good redox properties. The energy bandgaps of the polymers obtained from optical absorption spectra range from 2.1 to 2.3 eV. Among the polymers, poly[ N-butyl-2,7-di(2-(3,4-ethylenedioxthienyl))carbazole] shows the lowest bandgap energy of 2.1 eV, which is lower than that of previously reported poly(3,6-carbazole) analogues (2.4 eV). This polymer exhibits a significant color change from red in the oxidized state to blue in the reduced state during an electrochemical redox process. The electrochemical and optical properties of the monomers are dependent on external heteroaromatic rings attached to the 2 and 7 positions of the carbazole unit.

There are no comments yet on this publication. Be the first to share your thoughts.