Abstract
Abstract 6,7-Bis(hexylthio)-2-[(2-hydroxyethyl)thio]-3-methylthio-tetrathiafulvalene (TTF-2) is coupled with thiophene-3-carboxylic acid and thiophene-3,4-dicarboxylic acid by Steglich esterification, respectively, to afford 2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl thiophene-3-carboxylate (TTF-Th) and bis(2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl)thiophene-3,4-di-carboxylate (DTTF-Th). Their structures were characterized by ESI-MS, 1H NMR, and elemental analysis. Electropolymerization of TTF-Th and DTTF-Th was conducted with 0.1 M n-Bu4NPF6. The results indicated that both assemblies could rapidly form polymers via electrochemical deposition. In addition, their electrochromic performances illustrated that the color of P(TTF-Th) could switch from orange-yellow to dark blue, while P(DTTF-Th) changed its color from orange in the neutral state to dark blue in the oxidation state. Moreover, the electrochromic performances of P(DTTF-Th) were better than P(TTF-Th) due to the introduction of one extra TTF unit.
Highlights
6,7-Bis(hexylthio)-2-[(2-hydroxyethyl)thio]-3methylthio-tetrathiafulvalene (TTF-2) is coupled with thiophene-3-carboxylic acid and thiophene-3,4-dicarboxylic acid by Steglich esterification, respectively, to afford 2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3dithiolylidene)]-4-yl)thio)ethyl thiophene-3-carboxylate (TTF-Th) and bis(2-((4′,5′-bis(hexylthio)-5-(methylthio)[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl)thiophene-3,4di-carboxylate (DTTF-Th)
The results indicated that the polymers possessed electrochromic performances when different potentials were applied to them
The electrochemical redox behaviors of TTF-Th and DTTF-Th were examined by cyclic voltammetry at a potential scan rate of 100 mV s−1
Summary
Abstract: 6,7-Bis(hexylthio)-2-[(2-hydroxyethyl)thio]-3methylthio-tetrathiafulvalene (TTF-2) is coupled with thiophene-3-carboxylic acid and thiophene-3,4-dicarboxylic acid by Steglich esterification, respectively, to afford 2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3dithiolylidene)]-4-yl)thio)ethyl thiophene-3-carboxylate (TTF-Th) and bis(2-((4′,5′-bis(hexylthio)-5-(methylthio)[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl)thiophene-3,4di-carboxylate (DTTF-Th). Their structures were characterized by ESI-MS, 1H NMR, and elemental analysis. The results indicated that both assemblies could rapidly form polymers via electrochemical deposition Their electrochromic performances illustrated that the color of P(TTF-Th) could switch from orange-yellow to dark blue, while P(DTTFTh) changed its color from orange in the neutral state to dark blue in the oxidation state. By comparing the experimental results of different polymers, we can make a clear understanding of the influence of TTF numbers on electrochromic properties, which is the aim and the innovation of this study.
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