Electrochromic properties of multicolored novel polymer synthesized via combination of benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole units

Rende, Eda
Kilic, Cihan E.
Udum, Yasemin Arslan
Toffoli, Daniele
Toppare, Levent Kamil
Synthesis of new conducting polymers is desired since their electrochemical and optical properties enable them to be used as active layers in many device applications. Benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole (SNS Series) containing polymers showed very promising results as electrochromic materials. In order to observe the effect of the combination of these two units, three new monomers; 2-(6-(2,5-bis(5-methylthiophen-2-yl)-1H-pyrrol-1-yl)hexyl)-4,7-di(thiophen-2-yl)-2H benzo[d][1,2,3]triazole (M1), 2-(6-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)hexyl)-4,7-di(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole (M2) and 2-(6-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)hexyl)-4,7-bis(5-methylthiophen-2-y1)-2H-benzo[d][1,2,3]triazole (M3) were synthesized. To better characterize the electronic and spectroscopic properties of the monomers, density functional theory (DFT) and its time-dependent generalization (TD-DFT) were used to calculate their vertical ionization potentials, vertical electron affinity and to simulate and interpret their infrared and UV-vis spectra. The monomers were electrochemically polymerized and the resultant polymers were characterized with cyclic voltammetry and UV-vis-NIR spectroscopy techniques. An electrochromic device was constructed with electrochemical polymer of M2. The device switched between red and blue colors and showed exceptional optical memory.


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Baran, Derya; Toppare, Levent Kamil; Department of Chemistry (2010)
Organic semi-conductors are of great interest since these compounds can be utilized as active layers in many device applications such as ECDs, LEDs and solar cells. Incorporating the benzotriazole units into the polymer backbone enhances the optical properties of donor units. Hexyl thiophene and pyrrole are commonly used as electron donor materials. Benzotriazole can be coupled to hexyl thiophene or pyrrole to yield materials which can be polymerized to give donor acceptor type polymers. These materials are...
Citation Formats
E. Rende, C. E. Kilic, Y. A. Udum, D. Toffoli, and L. K. Toppare, “Electrochromic properties of multicolored novel polymer synthesized via combination of benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole units,” ELECTROCHIMICA ACTA, pp. 454–463, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41493.