A promising combination of benzotriazole and quinoxaline units: A new acceptor moiety toward synthesis of multipurpose donor-acceptor type polymers

Date

2012-01-01

Author

Ozdemir, Serife
Sendur, Merve
Oktem, Gozde
Doğan, Özdemir
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

116
views

0
downloads

By combining benzotriazole and quinoxaline units in an acceptor unit, three novel monomers, 2-dodecyl-6,7-diphenyl-4,9-di(thiophen-2-yl)-2H-[1,2,3] triazolo[4,5-g] quinoxaline (M-1), 2-dodecyl-4,6,7,9- tetra(thiophen-2-yl)-2H-[1,2,3] triazolo[4,5-g] quinoxaline (M-2) and 6,7-bis(4-tert-butylphenyl)-2- dodecyl-4,9-di(thiophen-2-yl)-2H-[1,2,3] triazolo[4,5-g] quinoxaline (M-3), were synthesized and polymerized electrochemically. All polymers revealed both p- and n-type doping properties under ambient conditions. As found by spectroelectrochemical studies they have small band gaps, ca. 1.00 eV. The polymers revealed two distinct absorption bands as all green coloured neutral state donor-acceptor donor type polymers should have. Besides this, all have broad absorptions covering the region between 700 nm and 1000 nm which is rarely seen in electrochromic polymers. Due to these promising features, they are considered to be potential materials for optoelectronics.

Subject Keywords

Low-Band-Gap, Electrochromic polymers, Conjugated polymers, Green, Matrix, State

URI

https://hdl.handle.net/11511/36216

Journal

JOURNAL OF MATERIALS CHEMISTRY

DOI

https://doi.org/10.1039/c2jm16171k

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Neutral-State Green Conjugated Polymers from Pyrrole Bis-Substituted Benzothiadiazole and Benzoselenadiazole for Electrochromic Devices Baran, Derya; Oktem, Gozde; Celebi, Selin; Toppare, Levent Kamil (2011-04-15) Two donor/acceptor/donor-type pyrrole-incorporated monomers, 4,7-di(1H-pyrrol-2-yl)benzo[c][1,2,5]thiadiazole (M1) and 4,7-di(1H-pyrrol-2-yl) benzo[c][1,2,5] selenadiazole (M2), were synthesized and polymerized electrochemically. The resulting polymers (P1 and P2) were investigated in terms of their electrochromic and optical properties. Spectroelectrochemistry studies revealed that both polymers show two distinct absorptions in both red and blue regions. The absorptions at around 400 and 700 nm correspond ...
Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor-acceptor-donor type polymers OZELCAGLAYAN, Ali Can; SENDUR, Merve; AKBASOGLU, Naime; APAYDIN, Dogukan Hazar; Çırpan, Ali; Toppare, Levent Kamil (2012-04-15) A new benzimidazole unit, 4'-(tert-butyl)spiro[benzo[d]imidazole-2,1'-cyclohexane] was synthesized and coupled with different donor units like 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT) via Stille coupling. The donor-acceptor-donor (D-A-D) type monomers, 4'-(tert-butyl)-4,7-bis(4-hexylthiophen-2-yl)spiro[benzo[d]imidazole-2,1'-cyclohexane] (BIHT) and 4'-(tert-butyl)-4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)spiro[benzo[d]imidazole-2,1'-cyclohexane] (BIED) were electrochemically polymerize...
The effect of changes in pi-conjugated terthienyl systems using thienyl and ethylenedioxybenzene functionalized thieno[3,4-b]pyrazine precursors: Multicolored low band gap polymers Tarkuc, Simge; Unver, Elif Kose; Udum, Yasemin Arslan; Tanyeli, Cihangir; Toppare, Levent Kamil (2010-10-01) New classes of thieno[3,4-b]pyrazines containing thienyl and ethylenedioxy phenyl units on electron-withdrawing moieties of pi-conjugated terthienyl were synthesized. The effect of structural differences on electrochemical and optoelectronic properties of the resulting polymers was investigated. Changes in the electronic nature of the functional groups enable to tune the electrochemical properties of the pi-conjugated terthienyl monomers by lowering oxidation potential from 062 V (DTTP) to 056 V (DBTP) Spec...
Synthesis and characterization of a polybenzoxazine from a difunctional amine and a trifunctional phenol Kaya, Şafak; Tinçer, Teoman; Department of Polymer Science and Technology (2009) Synthesis of a polymer with benzoxazine units in the main chain backbone by a trifunctional phenol, a difunctional amine, and paraformaldehyde was achieved. Thermal, mechanical and spectroscopic characterization and the viscosity properties of the synthesized polymer were studied. In the first step of this study, a fast and feasible method for the synthesis of the benzoxazine precursors was developed since some methods mentioned in the literature about the synthesis of the benzoxazine derivatives last long ...
Synthesis and characterization of thiophene functionalized polystyrene copolymers and their electrochemical properties Sahin, E; Camurlu, P; Toppare, Levent Kamil; Mercore, VM; Cianga, I; Yagci, Y (Wiley, 2005-12-01) Thiophene functionalized polystyrene samples (TFPS) were synthesized by atom transfer radical polymerization (ATRP) of styrene, followed by Suzuki coupling with 3-thiophene (Th) boronic acid. Conducting graft polymer of TFPS with thiophene was achieved at 1.5 V in tetrabutylammonium tetrafluoroborate/dichloromethane (TBAFB/DM) by electrochemical methods. Spectroelectrochemical analysis of the resulting copolymers [P(TFPS-co-Th)] reflected electronic transitions at 449, 721 and 880 nm, revealing pi - pi* tra...

Citation Formats

S. Ozdemir, M. Sendur, G. Oktem, Ö. Doğan, and L. K. Toppare, “A promising combination of benzotriazole and quinoxaline units: A new acceptor moiety toward synthesis of multipurpose donor-acceptor type polymers,” JOURNAL OF MATERIALS CHEMISTRY, pp. 4687–4694, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/36216.