Syntheses and Optical Properties of Perfluorophenyl Containing Benzimidazole Derivatives: The Effect of Donor Units

Abstract

Synthesis of two novel donor – acceptor – donor type monomers containing benzimidazole as the acceptor unit and thiophene and 3,4-ethylenedioxythiophene (EDOT) as the donor units were performed. 2-(Perfluorophenyl)-4,7-di(thiophen-2-yl)-1H-benzo[d]imidazole and 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-(perfluorophenyl)-1H-benzo[d]imidazole were synthesized successfully and polymerized electrochemically. The electrochemical and spectroelectrochemical studies of the polymers were studied. The effect of electron donating moieties on the optical properties of electrochemically polymerized polymers was investigated. Both polymers were p type dopable and possessed multi-chromic property. Optical studies demonstrated that the polymer based on EDOT unit (P2) resulted in lower band gap since EDOT is higher electron donating group than thiophene.

Keywords:

• Benzimidazole
• donor-acceptor
• donor effect
• perfluorophenyl
• electrochromism

Acknowledgements

The authors thank Cem Ozcan for the preparation of the graphical abstract and Seza Goker for the interpretation of NMR spectra. We thank Seda Comez for colorimetry studies.