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Synthesis and spectroelectrochemistry of dithieno(3,2‐ b :2′,3′‐ d )pyrrole derivatives
Author(s) -
Udum Yasemin Arslan,
Yıldız Hüseyin Bekir,
Azak Hacer,
Sahin Elif,
Talaz Oktay,
Çırpan Ali,
Toppare Levent
Publication year - 2014
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.40701
Subject(s) - electrochromism , alkyl , cyclic voltammetry , chemistry , polymer chemistry , pyrrole , electrochemistry , aryl , medicinal chemistry , organic chemistry , electrode
New π‐conjugated polymers containing dithieno(3,2‐ b :2′,3′‐ d )pyrrole (DTP) were successfully synthesized via electropolymerization. The effect of structural differences on the electrochemical and optoelectronic properties of the 4‐[4H‐dithieno(3,2‐b:2′,3′‐d)pyrrol‐4‐yl]aniline (DTP–aryl–NH 2 ), 10‐[4 H ‐dithiyeno(3,2‐ b :2′,3′‐ d )pirol‐4‐il]dekan‐1‐amine (DTP–alkyl–NH 2 ), and 1,10‐bis[4 H ‐dithieno(3,2‐ b :2′,3′‐ d )pyrrol‐4‐yl] decane (DTP–alkyl–DTP) were investigated. The corresponding polymers were characterized by cyclic voltammetry, NMR ( 1 H‐NMR and 13 C‐NMR), and ultraviolet–visible spectroscopy. Changes in the electronic nature of the functional groups led to variations in the electrochemical properties of the π‐conjugated systems. The electroactive polymer films revealed redox couples and exhibited electrochromic behavior. The replacement of the DTP–alkyl–DTP unit with DTP–aryl–NH 2 and DTP–alkyl–NH 2 resulted in a lower oxidation potential. Both the poly(10‐(4 H ‐Dithiyeno[3,2‐ b :2′,3′‐d]pirol‐4‐il)dekan‐1‐amin) (poly(DTP–alkyl–NH 2 )) and poly(1,10‐bis(4 H ‐dithieno[3,2‐ b :2′,3′‐ d ]pyrrol‐4‐yl) decane) (poly(DTP–alkyl–DTP)) films showed multicolor electrochromism and also fast switching times (<1 s) in the visible and near infrared regions. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131 , 40701.