Further investigation of intramolecular H-bonding in benzimidazole and EDOT containing monomer

Nurioglu, Ayda Goycek
Akpinar, Hava
Kanik, Fulya Ekiz
Toffoli, Daniele
Toppare, Levent Kamil
Density functional theory (OFT) calculations of the relative stabilities and harmonic vibrational spectra of four different conformers of 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-phenyl-1H-benzo[d] imidazole (BlmBEd) are presented and compared with experimental IR data. BlmBEd, containing phenyl substituted benzimidazole as the acceptor and 3,4-ethylenedioxythiophene (EDOT) as the donor unit, was electrochemically polymerized in different pH media earlier. Electronic states of nitrogen in benzimidazole unit of synthesized polymeric films were analyzed via X-ray photoelectron spectroscopy. Both DFT and XPS results suggest the presence of an intramolecular H-bond between the amine of the imidazole and the oxygen of the EDOT molecules. Additionally, the quantity of the H-bond can be controlled via treatment of an acid (trifloroacetic acid) and a base (sodium hydroxide) as we stated in our previous study.


Synthesis and characterization of optical, electrochemical and photovoltaic properties of selenophene bearing benzodithiophene based alternating polymers
Atli, Gulten Ozkul; Alemdar, Eda; Taşkaya Aslan, Sultan; Udum, Yasemin Arslan; Toppare, Levent Kamil; Çırpan, Ali (Elsevier BV, 2020-04-01)
In this study two donor-acceptor type alternating polymers containing electron-deficient benzotriazole moiety and electron-rich selenophene bearing benzodithiophene moiety; P1 and P2, were designed and synthesized via Stille polymerization. Moreover, the effects of thiophene and selenophene as pi-bridges on optical, electrochemical and optoelectronic features of polymers were examined. The optical band gap values of P1 and P2 were found as 1.47 eV and 1.72 eV, respectively. Cyclic voltammetry studies were p...
Molecular architecture: Another plausible pathway toward a low band gap polymer
Tarkuc, Simge; Udum, Yasemin Arslan; Toppare, Levent Kamil (Elsevier BV, 2010-05-01)
A donor-acceptor-donor pi-conjugated monomer (10,13-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)dibenzo[a,c]phenazine (PHED)) composed of bi-EDOT and dibenzo[a,c]phenazine repeat units was synthesized to examine the role of acceptor structure on the electronic and optoelectronic properties of the polymer. The spectroelectrochemical analysis showed that the introduction of electron-accepting unit results in a shift in the onset of the pi-pi* transition towards longer wavelengths. The optical band gap (Eg) f...
Tuning molecular energy levels and band gap of two-dimensional benzo[1,2-b:4,5-b '] dithiophene and quinoxaline bearing polymers
Yasa, Mustafa; Goker, Seza; Udum, Yasemin; Toppare, Levent Kamil (Elsevier BV, 2019-08-15)
Two novel donor-acceptor (D-A)-type two-dimensional (2-D) polymers of PBDTSeQ (P1) and PBDTFQ (P2) were synthesized and characterized where 4,8-bis[5-(2-ethylhexyl) thiophen-2-yl] benzo[1,2-b:4,5-b'] dithiophene (BDT) was used as the donor unit. 2,3-Bis(3,4-bis(octyloxy)phenyI)-5,8-dibromoquinoxaline was used as the acceptor moiety and selenophene and furan were utilized as n bridges. Optoelectronic properties of the polymers were examined by electrochemical and spectroelectrochemical characterizations. In ...
Orbey, H.; Orbey, N. (Informa UK Limited, 1989-3)
A data reduction technique is introduced for the evaluation of second virial coefficients of gases at subcritical temperatures. The method makes use of the vapor-liquid equilibrium data, i.e., temperature, saturation pressure, liquid and vapor molar volumes and can be used to obtain second virial coefficients of a wide variety of fluids including polar, associating and quantum gases. The calculated second virial coefficients are in good agreement with their counterparts from literature, which are obtained f...
Electrochemical and optical properties of novel terthienyl based azobenzene, coumarine and fluorescein containing polymers: Multicolored electrochromic polymers
Yigit, Deniz; Udum, Yasemin Arslan; GÜLLÜ, Mustafa; Toppare, Levent Kamil (Elsevier BV, 2014-01-01)
Three electroactive terthienyl based monomers, namely 1-phenyl-2-[4-(2,2':5',2 ''-terthien-3'-ylmethoxy)phenyl]diazene (TTAz), 4-(2,2':5',2 ''-terthien-3'-ylmethoxy)-2H-chromen-2-one (TTCo) and methyl 2-[3-oxo-6-(2,2':5',2 ''-terthien-3'-ylmethoxy)-3H-xanthen-9-yl] benzoate (TTFlo), were synthesized with good yields and their conducting polymers were electrochemically prepared on ITO electrode surfaces. The effect of chromophore type on electrochemical and optical properties of the polymers was investigated...
Citation Formats
A. G. Nurioglu, H. Akpinar, F. E. Kanik, D. Toffoli, and L. K. Toppare, “Further investigation of intramolecular H-bonding in benzimidazole and EDOT containing monomer,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 23–27, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35451.