Issue 5, 2015

Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications

Abstract

Three novel 2,5-dithienylpyrrole (SNS) derivatives containing strong chromophore units such as azobenzene, coumarin and fluorescein were synthesized to investigate the effects of chromophore substituents on the electrochemical and spectroelectrochemical properties of resulting polymers. Electrochemical and optoelectronic characteristics of the homopolymers, poly(1-(2-(4-(phenyldiazenyl)phenoxy)ethyl)-2,5-di(thiophen-2-yl)-1H-pyrrole) (PTPTAz), poly(4-(2-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)ethoxy)-2H-chromen-2-one) (PTPTCo) and poly(methyl 2-(6-(2-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)ethoxy)-3-oxo-3H-xanthen-9-yl)benzoate) (PTPTFlo), were investigated in detail. The combination of a strong chromophore pendant group with a poly(2,5-dithienylpyrrole) (PSNS) backbone significantly influences the electronic and optoelectronic behaviors of conducting polymers. PTPTAz and PTPTCo exhibited different colors in their neutral and oxidized states while PTPTFlo showed a yellow color in all states. The optical band gap (Eg) values of PTPTAz, PTPTCo and PTPTFlo films were calculated as 2.81 eV, 2.44 eV and 2.31 eV respectively. Moreover, a PTPTFlo/PEDOT based dual type solid state electrochromic device (ECD) was constructed. The ECD exhibited quite good long-term stability with reasonable optical memory performance under ambient conditions.

Graphical abstract: Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications

Article information

Article type
Paper
Submitted
21 Nov 2014
Accepted
19 Jan 2015
First published
19 Jan 2015

New J. Chem., 2015,39, 3371-3379

Author version available

Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications

D. Yiğit, Ş. O. Hacıoğlu, M. Güllü and L. Toppare, New J. Chem., 2015, 39, 3371 DOI: 10.1039/C4NJ02098G

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