Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor-acceptor-donor type polymers

APAYDIN, Dogukan Hazar
Çırpan, Ali
Toppare, Levent Kamil
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 polymerized, their electrochemical and optical properties were investigated by cyclic voltammetry, UV-vis-NIR spectroscopy techniques. Effect of donor groups on the optical and electronic properties of polymer was studied.


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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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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 a Luminol Based Chemiluminescent Trimeric System
Kesimal, Busra; Balci, Burcu; Çakal, Deniz; Önal, Ahmet Muhtar; Cihaner, Atilla (2023-01-01)
A luminol based chemiluminescent trimeric system, namely 2,3-dihydro-5,8-di(thiophen-2-yl)phthalazine-1,4-dione (T2B-Lum), bearing thiophene rings as donor units and 2,3-dihydrophthalazine-1,4-dione as an acceptor unit was synthesized in two steps via donor-acceptor-donor approach using two different methods. It was found that T2B-Lum emits chemiluminescent light when exposed to H2O2 in a basic medium, and the presence of substituents and the type of aromatic ring bearing chemiluminescent active group have ...
Influence of hydrogen bonding on electrochromic properties of conducting polymers
Akpinar, Hava; Nurioglu, Ayda Goycek; Toppare, Levent Kamil (2012-09-01)
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 duri...
Synthesis and optical properties of light-emitting π-conjugated polymers containing biphenyl and dithienosilole
LIAO, Liang; Çırpan, Ali; CHU, Qinghui; KARASZ, Frank E.; PANG, YI (Wiley, 2007-05-15)
Copolymers containing oligo(phenylene vinylene) (2.5), fluorene, and 4,4-dihexyldithienosilole (DTS) units were synthesized and characterized. The pi-conjugated monomers were joined with the palladium(0)-catalyzed Suzuki-Miyaura coupling reaction, thus forming either biphenyl- or phenyl-thiophene linkages. These polymers were photoluminescent, with the fluorescent quantum efficiency between 54 and 63% and with),lambda(max) for fluorescence at similar to 448 nm in tetrahydrofuran. The presence of 5% DTS in t...
Citation Formats
A. C. OZELCAGLAYAN, M. SENDUR, N. AKBASOGLU, D. H. APAYDIN, A. Çırpan, and L. K. Toppare, “Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor-acceptor-donor type polymers,” ELECTROCHIMICA ACTA, pp. 224–229, 2012, Accessed: 00, 2020. [Online]. Available: