Synthesis, photophysical and photovoltaic properties of 11- fluorodibenzo[a,c]phenazine bearing donor–acceptor type conjugated polymers

Aktaş, Ece
In this study, dibenzo[a,c]phenazine moiety was modified with fluorine atom to decrease the HOMO level of acceptor unit. Benzodithiophene derivative and dibenzosilole derivative were used as donor unit in the polymer backbone. In addition, 3-hexyltihophene was used as the π-bridge molecule with their donor character in polymer backbone. Also, 3,4-ethylenedioxythiophene was used to obtain new monomer to compare oxidation potential with 3-hexylthiophene based monomer. In this manner, two new conjugated monomers (PTFBPz and PEFBPz) and two new conjugated polymers (PBDT-FBPz and PBDT-TFBPz) were synthesized via Stille cross-coupling. In addition, the new conjugated polymer (PSi-TFBPz) was synthesized via Suzuki cross-coupling reactions. The electrochromic studies of all homopolymers and copolymers were performed and HOMO-LUMO energy levels of them were calculated. The absorption properties of polymers were investigated in solution and thin film. The photovoltaic studies of three polymers were performed. All photovoltaic devices were constructed with the conventional device structure (ITO/PEDOT:PSS/polymer:PCBM71/LiF/Al). In addition, the photovoltaic device fabrication and current-voltage characteristics of these devices were studied in an oxygen and moisture free glove box system. The power conversion efficiency (PCE) of conjugated polymers were measured under standard AM 1.5 Global illumination (100mW/cm2). The highest PCE values was found as 1.53% for PBDT-TFBPz, 1.12% for PBDT-FBPz and 0.58% for PSi-TFBPz.


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In this study, donor-acceptor random polymers containing benzotriazole acceptor and bistriphenylamine and benzodithiophene donors, P1 and P2, were successfully synthesized by Stille coupling polymerization. The effect of bistriphenylamine moiety and thiophene -conjugated linker on electrochemical, spectroelectrochemical, and optical behaviors of the polymers were investigated. Optoelectronic properties and photovoltaic performance of the polymers were examined under the illumination of AM 1.5G, 100 mWcm(-2)...
Synthesis, spectroscopic and electrochemical studies of perylene containing conjugated copolymers
Bayseç, Şebnem; Toppare, Levent Kamil; Yılmaz, Levent; Department of Polymer Science and Technology (2013)
The synthesis , spectroscopic and electrochemical properties of a series of donor-acceptor (DA) type polymers by changing the donor unit (thiophene, dithienopyrrole) polymer backbone were investigated.The synthesized CoP1 and CoP2 were designed to investigate the effect of copolymerization and insertion of perylene tetracarboxylic dimide (PDI) on the structure of benzotriazole (BTz) based polymers. For CoP1 1,7-dibromo-perylene diimide,4,7-dibromo-2-dodecyl-2H-benzo[d][1,2,3]triazole and 2,5 bis(tributylsta...
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...
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 of New Thienylene Pyrrole Monomers and Their Electropolymerizations
Eken, Serap; Carbas, Buket Bezgin; Akdağ, Akın; Önal, Ahmet Muhtar (The Electrochemical Society, 2014-01-01)
In this study, four new 2,5-dithienylpyrroles (SNS) 1-(3-fluoro-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-FPTP), 1-(3-chlorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-ClPTP), 1-(3-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-BrPTP) and 1-(4-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (p-BrPTP) containing meta and para substituted benzene ring at the nitrogen atom were synthesized via Paal-Knorr condensation of 1,4-di(2-thienyl)-1,4-butanedione with corresponding halo-substituted anilines. The mon...
Citation Formats
E. Aktaş, “Synthesis, photophysical and photovoltaic properties of 11- fluorodibenzo[a,c]phenazine bearing donor–acceptor type conjugated polymers,” M.S. - Master of Science, Middle East Technical University, 2016.