Influence of hydrogen bonding on electrochromic properties of conducting polymers

Date

2012-09-01

Author

Akpinar, Hava
Nurioglu, Ayda Goycek
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

166
views

0
downloads

4,7-Bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-phenyl-1H-benzo[d]imidazole (BImBEd) was synthesized via Stille coupling reaction of 4,7-dibromo-2-phenyl-1H-benzo[d]imidazole (BImB) with monostannylated 3,4-ethylenedioxythiophene (EDOT). In order to figure out the presence of an intramolecular hydrogen bonding between the amine bond of the imidazole ring and the oxygen of the EDOT molecule, different amounts of trifluoroacetic acid (TFA) and concentrated sodium hydroxide (NaOH) solutions were added during electrochemical polymerization. These treatments caused protonation of the imine and deprotonation of the amine bonds respectively. In order to prove the changes in the optical properties of the polymers due to different number of protonated and deprotonated imine and amine bonds, 1,4-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzene (BEDOT-B) was also synthesized. Results showed that it is possible to control the main chain conformation of even an insoluble polymer via acid and base treatments during in situ polymerization.

Subject Keywords

Hydrogen bonding, Benzimidazole, Electrochromism, Conjugated polymers

URI

https://hdl.handle.net/11511/48103

Journal

JOURNAL OF ELECTROANALYTICAL CHEMISTRY

DOI

https://doi.org/10.1016/j.jelechem.2012.08.001

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

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 impact of [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole structure on the optoelectronic properties of conjugated polymers Alkan, Ecem Aydan; GÖKER, SEZA; Sarigul, Hatice; Yıldırım, Erol; Udum, Yasemin Arslan; Toppare, Levent Kamil (2020-04-01) Two novel conjugated near-infrared (NIR) absorbing donor-acceptor type copolymers comprising benzodithiophene as the donor and [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole derivatives as the acceptors, spaced with thiophene as the pi-bridge, were designed and synthesized via Stille polycondensation reaction. The effect of acceptor strength on optoelectronic properties was targeted and investigated. Branched alkyl chains (the extended 2-octyl-1-dodecyl alkyl chain; -C8C12) were introduced to 5H-[1,2,3]t...
Influence of the sol-gel preparation method on the photocatalytic NO oxidation performance of TiO2/Al2O3 binary oxides Polat, Meryem; Soylu, Asli M.; Altunöz Erdoğan, Deniz; Erguven, Huseyin; Vovk, Evgeny I.; Ozensoy, Emrah (2015-03-01) In the current work, TiO2/Al2O3 binary oxide photocatalysts were synthesized via two different sol-gel protocols (P1 and P2), where various TiO2 to Al2O3 mole ratios (0.5 and 1.0) and calcination temperatures (150-1000 degrees C) were utilized in the synthesis. Structural characterization of the synthesized binary oxide photocatalysts was also performed via BET surface area analysis, X-ray diffraction (XRD) and Raman spectroscopy. The photocatalytic NO(g) oxidation performances of these binary oxides were m...
Synthesis, characterization and electrochromic properties of conducting copolymers of terephthalic acid bis-(thiophen-3-ylmethyl)thioester with thiophene and pyrrole and conducting polymer of 1-(4-fluorophenyl)-2,5-di(thiophen-2-yl)-1h-pyrrole Türkarslan, Özlem; Toppare, Levent Kamil; Department of Chemistry (2006) Terephthalic acid bis-(thiophen-3-ylmethyl)thioester (TTMT) was synthesized via the reaction of thiophen-3-ylmethanethiol with terephthaloyl dichloride. Nuclear magnetic resonance (1H-NMR) and Fourier transform infrared (FTIR) spectroscopies were utilized for the characterization of the monomer. This 3-functionalized thiophene monomer was polymerized in the presence of thiophene (Th) and pyrrole (Py) upon constant potential application in acetonitrile/tetrabutylammonium tetrafluoroborate (TBAFB). The result...
EFFECT OF π-BRIDGES ON ELECTROCHEMICAL AND PHOTOVOLTAIC PROPERTIES OF BENZOTHIADIAZOLE AND BENZODITHIOPHENE BASED CONJUGATED POLYMERS Dikbıyık, Dilan Ece; Çırpan, Ali; Hızalan Özsoy, Gönül; Department of Chemistry (2022-1-28) In this study, a series of the Donor -π bridge- Acceptor type conjugated polymers (PT1, PT2, and PT3) were designed and synthesized via Pd-catalyzed Stille polycondensation reactions. Synthesized polymers were used as donor moieties and blended with acceptor unit PC71BM to form the active layer of the bulk heterojunction organic solar cell (BHJ OSC). Polymers contain electron-deficient benzothiadiazole (BT) as acceptor unit and electron-rich benzodithiophene (BDT) as donor unit. Moreover, thiophene [T], sel...

Citation Formats

H. Akpinar, A. G. Nurioglu, and L. K. Toppare, “Influence of hydrogen bonding on electrochromic properties of conducting polymers,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 62–69, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/48103.