Synthesis and spectroelectrochemistry of dithieno(3, 2‐b:2′, 3′‐d)pyrrole derivatives. Issue 17 (17th April 2014)

• Record Type: Journal Article
• Authors: Udum, Yasemin Arslan; Yıldız, Hüseyin Bekir; Azak, Hacer; Sahin, Elif; Talaz, Oktay; Çırpan, Ali; Toppare, Levent
• Is Part Of: Journal of applied polymer science. Volume 131:Issue 17(2014:Sep. 05)
• Page Start: 8676
• Page End: 8683
• Publication Date: 2014-04-17
• Subjects: Polymers -- Periodicals; Polymerization -- Periodicals; 668.9
• DOI: 10.1002/app.40701
• Languages: English
• ISSNs: 0021-8995

Abstract

<abstract abstract-type="main"> <title>ABSTRACT</title> <p>New π‐conjugated polymers containing dithieno(3, 2‐<italic>b</italic>:2′, 3′‐<italic>d</italic>)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<sub>2</sub>), 10‐[4<italic>H</italic>‐dithiyeno(3, 2‐<italic>b</italic>:2′, 3′‐<italic>d</italic>)pirol‐4‐il]dekan‐1‐amine (DTP–alkyl–NH<sub>2</sub>), and 1, 10‐bis[4<italic>H</italic>‐dithieno(3, 2‐<italic>b</italic>:2′, 3′‐<italic>d</italic>)pyrrol‐4‐yl] decane (DTP–alkyl–DTP) were investigated. The corresponding polymers were characterized by cyclic voltammetry, NMR (<sup>1</sup>H‐NMR and <sup>13</sup>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<sub>2</sub> and DTP–alkyl–NH<sub>2</sub> resulted in a lower oxidation potential. Both the poly(10‐(4<italic>H</italic>‐Dithiyeno[3, 2‐<italic>b</italic>:2′, 3′‐d]pirol‐4‐il)dekan‐1‐amin) (poly(DTP–alkyl–NH<sub>2</sub>)) and poly(1, 10‐bis(4<italic>H</italic>‐dithieno[3, 2‐<italic>b</italic>:2′, 3′‐<italic>d</italic>]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. <bold>2014</bold>, <italic>131</italic>, 40701.</p> </abstract>