Syntheses and Optical Properties of Perfluorophenyl Containing Benzimidazole Derivatives: The Effect of Donor Units

ILERI, Merve
Çırpan, Ali
Toppare, Levent Kamil
Synthesis of two novel donor - acceptor - donor type monomers containing benzimidazole as the acceptor unit and thiophene and 3,4-ethylenedioxythiophene (EDOT) as the donor units were performed. 2-(Perfluorophenyl)-4,7-di(thiophen-2-yl)-1H-benzo[d]imidazole and 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-(perfluorophenyl)-1H-benzo[d]imidazole were synthesized successfully and polymerized electrochemically. The electrochemical and spectroelectrochemical studies of the polymers were studied. The effect of electron donating moieties on the optical properties of electrochemically polymerized polymers was investigated. Both polymers were p type dopable and possessed multi-chromic property. Optical studies demonstrated that the polymer based on EDOT unit (P2) resulted in lower band gap since EDOT is higher electron donating group than thiophene.


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Akbayrak, Merve; Önal, Ahmet Muhtar; Department of Chemistry (2016)
This study consists of synthesis of alternating donor-acceptor type hybrid monomers based on various carbazole units as the electron rich donor group and thieno[3,4c]pyrrole-4,6-dione (TPD) or 2,5-dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4dione (DPP) as the electron poor acceptor unit. The main goal of this research was not only to synthesize new low band gap polymers but also to shed more light on the substituent and linkage side effect of carbazole units on the optoelectronic properties of monomer...
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...
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Gunes, Arzu; CİHANER, ATİLLA; Önal, Ahmet Muhtar (2013-02-01)
A novel series of hybrid monomers containing furan and fluorene units, namely 2-(2-(furan-2-yl)-9H-fluoren-7-yl)furan (FFF), 2,7-di(furan-2-yl)-9H-fluoren-9-one (FOF) and 2-(2-(furan-2-yl)-9,9-dihexyl-9H-fluoren-7-yl)furan (FHF), was synthesized and their electrochemical polymerization was achieved via potential cycling. Optical and electrochemical properties of the polymers, poly(2-(2-(furan-2-yl)9H-fluoren-7-yl)furan (PFFF), poly(2,7-di(furan-2-yl)-9H-fluoren-9-one) (PFOF) and poly(2-(2-(furan2-yl)-9,9-di...
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Göksu, Kardelen.; Çırpan, Ali; Department of Chemistry (2019)
Two random terpolymers, PBTS and PBTSe were designed and synthesized successfully as the donor units for polymer organic solar cell. Desired terpolymers contain alkoxy-benzodithiophene as an electron rich unit and Noctylthieno[3,4,c]pyrrole-4,6-dione (TPD) as the electron deficient group. Furthermore, thiophene and selenophene π bridges were introduced to benzotriazole unit as the acceptor moieties into copolymer backbone. The properties of synthesized terpolymers solar cell device were investigated by opti...
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Eken, S.; Ergun, E. G. Cansu; Önal, Ahmet Muhtar (The Electrochemical Society, 2016-01-01)
Three new donor-acceptor-donor (DAD) type monomers containing five membered heteroaromatic rings as the donor units and the silicon-bridged bithiophene as the acceptor unit were synthesized via Stille cross-coupling reaction. The monomers, 2,6-di(furan-2-yl)-4,4-dioctyl-4H-silolo[3,2-b:4,5-b'] dithiophene (FSiF), 4,4-dioctyl-2,6-di(thiophen-2-yl)-4H-silolo[3,2-b:4,5-b']dithiophene (TSiT) and 4,4-dioctyl-2,6-di(selenophen-2-yl)-4H-silolo[3,2-b:4,5-b'] dithiophene (SeSiSe) were polymerized electrochemically v...
Citation Formats
M. ILERI, S. O. HACIOGLU, A. Çırpan, and L. K. Toppare, “Syntheses and Optical Properties of Perfluorophenyl Containing Benzimidazole Derivatives: The Effect of Donor Units,” JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY, pp. 510–516, 2015, Accessed: 00, 2020. [Online]. Available: