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
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 cyclic voltammetry (CV) studies, both polymers were found to be ambipolar. In anodic region, oxidation potentials were observed as 1.45 V and 1.15 V for P1 and P2 respectively, while reduction potentials were 0.65 V and 0.92 V. In cathodic region, redox potentials were found to be -1.36 V/-1.32 V and -2.0 V/-1.51 V for P1 and -1.45 V/-1.05 V and -2.15 V/-1.45 V for P2. Both polymers showed good solubility in common solvents. The synthesized polymers were used as photoactive layers in solar cell devices. P1-based device (ITO/PEDOT:PSS/P1:PC71BM (1:3, w/w)/LiF/Al) provided the best performance with a PCE of 4.04%, a V-OC of 0.67 V, a Jsc of 13.94 mA/cm(2), and a FF of 43.3%.


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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...
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...
Synthesis and polymerization of 2-and 3-substituted thiophene derivatives linked by polyether bridges
Tirkeş, Süha; Önal, Ahmet Muhtar (Elsevier BV, 2004-11-15)
New compounds consisting of 2- and 3-thienyl units linked by polyether bridges have been synthesized and their electrochemical polymerization was performed via constant potential electrolysis (CPE) in an electrolytic solution containing 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF(6)) dissolved in CH3CN. 2-Thienyl monomers (I and II), but not 3-thienyl monomers (III and IV), were also polymerized via chemical oxidation, which yielded broken pi-conjugated polymer products. The polymers were characteri...
Synthesis and spectroelectrochemical characterization of multi-colored novel poly(3,6-dithienylcarbazole) derivatives containing azobenzene and coumarin chromophore units
Yigit, Deniz; Hacioglu, Serife O.; GÜLLÜ, Mustafa; Toppare, Levent Kamil (Elsevier BV, 2016-04-01)
Azobenzene and coumarin units bearing four novel 3,6-linked thiophene-carbazole-thiophene type electroactive monomers were synthesized in order to observe the effects of strong chromophore units on the electrochemical and spectroelectrochemical behaviors of resulting pi-conjugated conducting polymers (PTCbzAz, PECbzAz, PTCbzCo and PECbzCo). Electronic and optoelectronic properties of all polymers were investigated by cyclic voltammetry and in situ spectroelectrochemical studies, and their oxidation potentia...
Spectroelectrochemical investigation of the anodic oxidation of dibenzo-18-crown-6
Cihaner, A; Önal, Ahmet Muhtar (Elsevier BV, 2004-10-01)
Poly(dibenzo-18-crown-6) (poly-DB18C6) was synthesized by electrochemical oxidation of dibenzo-18-crown-6 (DB18C6) using a mixture of acetonitrile and dichloromethane as the solvent and tetrabutylammonium tetrafluoroborate (TBABF(4)) or tetrabutylammonium hexafluorophosphate (TBAPF(6)) as supporting electrolyte. The anodic polymerization of DB18C6 was investigated using in situ ESR and in situ UV-Vis spectroscopic techniques. Spectroelectrochemical (SPEL), properties and thermal analysis of the resulting po...
Citation Formats
M. Yasa, S. Goker, Y. Udum, and L. K. Toppare, “Tuning molecular energy levels and band gap of two-dimensional benzo[1,2-b:4,5-b ’] dithiophene and quinoxaline bearing polymers,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 0–0, 2019, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/39786.