Multichromic polymers of benzotriazole derivatives: Effect of benzyl substitution

Date

2011-02-01

Author

Yigitsoy, Basak
Karim, S. M. Abdul
Balan, Abidin
Baran, Derya
Toppare, Levent Kamil

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

192
views

0
downloads

Two electroactive monomers 1-benzyl-4,7-di(thiophen-2-yl))-2H-benzo[d][1,2,3]triazole (BBTA) and 2-benzyl-4,7-di(thiophen-2-yl))-2H-benzo[d][1,2,3]triazole (BBTS) were synthesized with satisfactory yields. The effect of substitution site on electrochemical and optical properties was investigated with cyclic voltammetry and spectroelectrochemical studies. Results showed that position of pendant group alters the electronic structure of the resulting polymer causing different optical and electrochemical behaviors. Symmetrically positioned benzyl unit on benzotriazole moiety resulted in a neutral state red polymer. PBBTS, having multi-colored property in its different oxidized and reduced states. Its analogue PBBTA exhibited maximum absorption at 390 nm in its neutral state and also revealed multicolored electrochromic property upon stepwise oxidation. Very different optical band gap values were calculated: 1.55 eV and 2.25 eV for PBBTS and PBBTA, respectively.

Subject Keywords

Electrochemistry, General Chemical Engineering

URI

https://hdl.handle.net/11511/39957

Journal

ELECTROCHIMICA ACTA

DOI

https://doi.org/10.1016/j.electacta.2010.11.052

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Electrochromic properties of a novel low band gap conductive copolymer Yigitsoy, Basak; Varis, Serhat; Tanyeli, Cihangir; Akhmedov, Idris M.; Toppare, Levent Kamil (Elsevier BV, 2007-07-10) A copolymer of 2,5-di(thiophen-2-yl)-1-p-tolyl-1H-pyrrole (DTTP) with 3,4-ethylene dioxythiophene (EDOT) was electrochemically synthesized. The resultant copolymer P(DTTP-co-EDOT) was characterized via cyclic voltammetry, FTIR, SEM, conductivity measurements and spectroelectrochemistry. Copolymer film has distinct electrochromic proper-ties. It has four different colors (chestnut, khaki, camouflage green, and blue). At the neutral state; gimel(max) due to the pi-pi* transition was found to be 487 nm and E-g...
Electrochemical and optical properties of novel terthienyl based azobenzene, coumarine and fluorescein containing polymers: Multicolored electrochromic polymers Yigit, Deniz; Udum, Yasemin Arslan; GÜLLÜ, Mustafa; Toppare, Levent Kamil (Elsevier BV, 2014-01-01) Three electroactive terthienyl based monomers, namely 1-phenyl-2-[4-(2,2':5',2 ''-terthien-3'-ylmethoxy)phenyl]diazene (TTAz), 4-(2,2':5',2 ''-terthien-3'-ylmethoxy)-2H-chromen-2-one (TTCo) and methyl 2-[3-oxo-6-(2,2':5',2 ''-terthien-3'-ylmethoxy)-3H-xanthen-9-yl] benzoate (TTFlo), were synthesized with good yields and their conducting polymers were electrochemically prepared on ITO electrode surfaces. The effect of chromophore type on electrochemical and optical properties of the polymers was investigated...
Syntheses of electroactive layers based on functionalized anthracene for electrochromic applications Yıldırım, Ahmet; Tarkuc, S.; AK, MESUT; Toppare, Levent Kamil (Elsevier BV, 2008-05-30) A new monomer (DTAT) was synthesized via linking 3,4-ethylenedioxythiophene (EDOT) on anthracene. The polymer, P(DTAT) was electrosynthesized by anodic oxidation of the corresponding monomer in 0.1 M LiClO4 acetonitrile (ACN) solution. The optical properties, the absorption spectra and the kinetics, were examined. Spectroelectrochemical analysis showed that P(DTAT) has an electronic band gap (due to pi-pi* transition) of 1.57 eV at 776 nm.
Electrochemical polymerization of a new low-voltage oxidized thienylenepyrrole-derivative and its electrochromic device application Carbas, Buket Bezgin; KIVRAK, Arif; TEKE, Ecem; Zora, Metin; Önal, Ahmet Muhtar (Elsevier BV, 2014-09-01) Synthesis of a new monomer, 2,5-bis-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1-phenyl-1H-pyrrole (ENE), from pyrrole, iodobenzene and 3,4-ethylenedioxythiophene (EDOT), and its electropolymerization are reported. ENE was oxidized at a low oxidation potential (0.45 V vs. Ag/AgCl) and successfully electropolymerized in acetonitrile containing 0.1 M NaClO4 and LiClO4 electrolyte mixture. The resulting polymer, P(ENE), revealed five distinctive colors upon doping, which indicated that the polymer is multichro...
Dual type complementary colored polymer electrochromic devices utilized by 3-ester substituted thiophenes CAMURLU, P; Çırpan, Ali; Toppare, Levent Kamil (Elsevier BV, 2004-10-15) Dual type polymer electrochromic devices (ECDs) based on potentiodynamically coated films of octanoic acid 2-thiophen-3-yl-ethyl ester (OTE), decanedioic acid bis-(2-thiophen-3-yl-ethyl) ester (DATE) and ethylene dioxythiophene (EDOT) were constructed. The former two function as anodically coloring layers and the latter as a cathodically coloring layer in between tetrabutylammonium tetrafluoroborate (TBAFB) poly(methylmethacrylate) gel media. The spectroelectrochemistry, switching ability and stability of t...

Citation Formats

B. Yigitsoy, S. M. A. Karim, A. Balan, D. Baran, and L. K. Toppare, “Multichromic polymers of benzotriazole derivatives: Effect of benzyl substitution,” ELECTROCHIMICA ACTA, pp. 2263–2268, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/39957.