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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CETIN, Asli; ISTANBULLUOGLU, Cagla; HACIOGLU, Serife Ozdemir; CEVHER, ŞEVKİ CAN; Toppare, Levent Kamil; Çırpan, Ali (2017-11-15)
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, characterizations and photovoltaic applications of dithienothiophene and benzotriazole containing conjugated polymers
Cevher, Şevki Can; Çırpan, Ali; Toppare, Levent Kamil; Department of Chemistry (2013)
Fused bithiophene containing conjugated polymers are recently used in different applications; for example organic light emitting diodes, solar cells, electrochromic devices and organic field effect transistors. Fused bithiophene derivatives increase the planarity, charge mobility and decrease band gap when incorporated into the polymer backbone. Connecting atom between the bithiopheneunit can be phosphorous, silicon, nitrogen and sulphur. In this thesis, dihienothiophene was coupled with benzotriazole via S...
Synthesis and characterization of novel quinoxalinebased and thieno[3,4-c]pyrrole-4,6-dione-based conjugated polymers and their applications in organic electronics
Karabağ, Aliekber; Günbaş, Emrullah Görkem; Department of Polymer Science and Technology (2017)
In this thesis novel quinoxaline-based and thieno[3,4-c]pyrrole-4,6-dione (TPD)- based monomers were firstly synthesized. Structural analysis of each material synthesized was performed with Nuclear Magnetic Resonance (NMR) Spectroscopy and High-Resolution Mass Spectroscopy (HRMS). Two novel quinoxaline-based monomers were polymerized with electrochemical and/or chemical polymerization whereas TPD-based monomer was polymerized with benzodithiophene-based acceptor via Stille coupling polycondensation reaction...
synthesis of a novel series of furan and fluorene containing monomers and their polymers
Güneş, Arzu; Önal, Ahmet Muhtar; Cihaner, Atilla; Department of Polymer Science and Technology (2011)
In this study, a novel series of conjugated monomers containing furan and fluorene units; 2,7-di(furan-2-yl)-9H-fluoren-9-one (FOF), 2-(2-(furan-2-yl)-9H-fluoren-7-yl)furan (FFF), and 2-(2-(furan-2-yl)-9,9-dihexyl-9H-fluoren-7-yl)furan (FHF) were synthesized and their electrochemical polymerization were achieved via potential cycling. Optical and electrochemical properties of the polymers, poly(2,7-di(furan-2-yl)-9H-fluoren-9-one) (PFOF), poly(2-(2-(furan-2-yl)-9H-fluoren-7-yl)furan (PFFF) and poly(2-(2-(fu...
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...
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.