Synthesis of benzimidazole containing donor acceptor electrochromic polymers

Akpınar, Hava Zekiye
Donor-acceptor-donor (DAD) type benzimidazole (BIm) and 3,4-ethylenedioxythiophene (EDOT) bearing monomers (4-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-(2,3 dihydrothieno[3,4b][1,4] dioxin-7-yl)-2-benzyl-1H-benzo[d]imidazole (M1), 2,4-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)-1H-benzo[d]imidazole (M2) and 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)-2-ferrocenyl-1H-benzo[d]imidazole (M3)) were synthesized and electrochemically polymerized. Pendant group at 2-C position of the imidazole ring was functionalized with phenyl (P1), EDOT (P2) and ferrocene (P3) in order to observe substituent effect on electrochemical and electrochromic properties of corresponding polymers. Spectroelectrochemical results showed that different pendant groups resulted in polymers with slightly different optical band gaps (1.75, 1.69 and 1.77 eV respectively) and different number of achievable colored states. Optoelectronic performance were reported in detail. Keywords: Benzimidazole, EDOT, Donor-Acceptor Type Polymers, Electrochromism, Conjugated Polymers.


Synthesis and Characterization of Conducting Copolymers of Quinoxaline Derivatives
Turac, Ersen; Sahmetlioglu, Ertugrul; Toppare, Levent Kamil; Yuruk, Huseyin (Wiley, 2011-05-05)
Electrochemical copolymerizations of 2,3-di(2-thienyl)quinoxaline (M1), 6-methyl-2,3-di(2-thienyl)quinoxaline (M2), and 2,3-di(2-thienyl)quinoxaline-6-yl)(phenyl)methanone (M3) with 3,4-ethylenedioxy thiophene (EDOT) were carried out in CH3CN/TBABF(4) (0.1M) solvent-electrolyte couple via potentiodynamic electrolysis. The obtained copolymers were characterized by cyclic voltammetry (CV), Fourier transform-infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and thermogravimetry analyses (TGA). ...
Synthesis of new donor-acceptor polymers containing thiadiazoloquinoxaline and pyrazinoquinoxaline moieties: low-band gap, high optical contrast, and almost black colored materials
Unver, Elif Kose; Tarkuc, Simge; BARAN, Derya; Tanyeli, Cihangir; Toppare, Levent Kamil (Elsevier BV, 2011-05-25)
Two low band gap conjugated polymers, poly[4,9-bis(4-hexylthien-2-yl)-6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline] (PHTTQ) and poly[5,10-bis(4-hexylthien-2-yl)-2,3,7,8-tetra(thien-2-yl)pyrazino[2,3-g]quinoxaline] (PHTPQ), consisting of alternating electron-rich 3-hexylthiophene and electron-deficient 6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TTQ) and 2,3,7,8-tetra(thien-2-yl)-2,3-dihydropyrazino[2,3-g]quinoxaline (TPQ) units were synthesized electrochemically. The structures of th...
Synthesis of polythiophene and polypyrrole derivatives and their application in electrochromic devices
Ak, Metin; Toppare, Levent Kamil; Department of Chemistry (2006)
Different substituted thiophene and pyrrole monomers namely hexamethylene (bis-3-thiopheneacetamide) (HMTA), N-(4-(3-thienylmethylene)-oxycarbonylphenyl)maleimide (MBThi), 2,4,6-Tris-(4-pyrrol-1-yl-phenoxy)-[1,3,5]triazine (TriaPy), 2,4,6-Tris-(thiophen-3-ylmethoxy)-[1,3,5] triazine (TriaTh), and N-(2-(thiophen-3-yl)methylcarbonyloxyethyl) maleimide (NMT) were synthesized. The chemical structures of the monomers were characterized by Nuclear Magnetic Resonance (1H-NMR and 13C-NMR) and Fourier Transform Infr...
Synthesis and mesophase properties of block and random co-polymers of electroactive and liquid crystalline monomers
Yilmaz, F; Kasapoglu, F; Hepuzer, Y; Yagci, Y; Toppare, Levent Kamil; Fernandes, EG; Galli, G (Informa UK Limited, 2005-01-01)
Homo-polymers and random co-polymers of electroactive and liquid crystalline monomers, namely 3-thienylmethyl methacrylate (MTM) and 6-(4-cyanobiphenyl-4'-oxy)hexyl acrylate (LC6), were prepared by conventional free radical polymerization. Block co-polymers of MTM and LC6 were also synthesized by using the 1,1-diphenylethene (DPE) method. The obtained random and block co-polymers exhibited liquid crystal behavior depending on the content of the LC6 units. It was found that microphase separation of the polym...
Synthesis and characterization of conducting copolymers of thiophene ended poly(ethyleneoxide) : their electrochromic properties and use in enzyme immobilization
Yıldız, Hüseyin Bekir; Toppare, Levent Kamil; Department of Chemistry (2007)
Thiophene ended poly(ethylene oxide) (ThPEO) and random copolymer (RPEO) of 3-methylthienyl methacrylate and p-vinylbenzyloxy poly (ethyleneoxide) units were synthesized chemically. Further graft copolymerization of RPEO and ThPEO with pyrrole (Py) and thiophene (Th) were achieved in H2O - sodium dodecylsulfate (SDS), H2O - p-toluenesulphonic acid (PTSA) and acetonitrile (AN) - tetrabutylammonium tetrafluoroborate (TBAFB) solvent electrolyte couples via constant potential electrolyses. Characterizations wer...
Citation Formats
H. Z. Akpınar, “Synthesis of benzimidazole containing donor acceptor electrochromic polymers,” M.S. - Master of Science, Middle East Technical University, 2011.