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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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...
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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)...
Syntheses and optoelectronic applications of thiadiazolo quinoxaline bearing alternating conjugated copolymers
Ataoğlu, Emre; Çırpan, Ali; Ünalan, Hüsnü Emrah; Department of Polymer Science and Technology (2016)
Donor-acceptor type conjugated polymers containing thiadiazolo quinoxaline and benzodithiophene derivatives were used as photoactive material for organic solar cell. The alkoxy- substituted benzo[1,2-b;4,5-b’]dithiophene (BDT) monomer, 2,6bis(trimethyltin)-4,8-di(2-ethylhexyloxyl)benzo[1,2-b;4,5-b’]dithiophene, was polymerized with 4,9-dibromo-[1,2,5]thiadiazolo[3,4-g]quinoxaline through a Pd(0)catalyzed Stille coupling reaction. In order to improve the interchain interactions between polymer chains, an alk...
Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications
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A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were perfor...
Synthesis and electrochemical polymerization of diketopyrrolopyrrole based donor-acceptor-donor monomers containing 3,6-and 2,7-linked carbazoles
Akbayrak, Merve; Önal, Ahmet Muhtar (2016-01-01)
Three new donor-acceptor-donor (D-A-D) type monomers bearing 2,7- or 3,6-linked carbazoles as the donor unit and 2,5-dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) as the electron poor acceptor unit were synthesized via a Suzuki cross coupling reaction. The monomers were electrochemically polymerized both by repetitive cycling and by constant potential electrolysis in acetonitrile-tetrabutylammonium hexafluorophosphate electrolytic medium containing boron trifluoride diethyl etherate (BFEE)....
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.