Investigation of Optical and Electrochemical Properties of Benzene Based Solution Processable 2,1,3-Benzooxadiazole Comprising Polymers

Hizalan, Gonul
Hacioglu, Serife O.
Toppare, Levent Kamil
Four novel solution processable benzooxadiazole containing alternating copolymers namely poly (5,6-bis(octyloxy)-4-(5-phenylthiophen-2-yl)-7-(thiophen-2-yl)benzo[c][1,2,5]oxadiazole)PBOTPh, poly (5,6-bis(octyloxy)-4-(5-phenylselenophen-2-yl)-7-(selenophen-2-yl)benzo[c][1,2,5]oxadiazole)PBOSPh, poly (4-(furan-2-yl)-5,6-bis(octyloxy)-7-(5-phenylfuran-2-yl)benzo[c][1,2,5]oxadiazole)PBOFPh and poly (5,6-bis(octyloxy)-4-(5-phenylthieno[3,2-b]thiophen-2-yl)-7-(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]oxadiazole) PBOTTPh incorporating 5,6-bis(octyloxy)benzo[c][1,2,5]oxadiazole as the acceptor moiety and benzene as the donor moiety were synthesized via Suzuki polycondensation reaction. Various electron donor moieties were used as pi bridges in the polymer backbone to tailor the optoelectronic properties of the polymers. To explore the electrochemical and electrochromic properties and the photovoltaic properties of the copolymers, cyclic voltammetry, spectroelectrochemistry and kinetic studies were conducted. Thiophene, selenophene, furan and thienothiophene pi bridges were incorporated into the polymer backbones. Thiophene and selenophene based alternating copolymers showed purple color in its neutral state whereas furan and thienothiophene bearing copolymers have pinkish purple and dark purple in their neutral states respectively. The optical band gaps of the polymers were calculated as 1.85, 1.76, 1.58, 1.79 eV for thiophene, selenophene, thienothiophene and furan based copolymers, respectively. Among all the alternating copolymers, the lowest optical band gap corresponds to thienothiophene comprising alternating copolymer which is 1.58 eV and red shifted in absorption due to the stronger donor character compared to other analogs. HOMO and LUMO levels were calculated from cyclic voltammetry studies using onsets of oxidation and reduction, respectively. HOMO levels were calculated as -5.96 eV for PBOTPh, -5.85 eV for PBOSPh, -5.63 eV for PBOTTPh and -5.74 eV for PBOFPh. LUMO levels were determined as -4.02 eV for PBOSPh, -4.03 eV for PBOTTPh and -3.87 eV for PBOFPh. Bulk heterojunction (BHJ) polymer solar cells based on selenophene containing polymer were fabricated. The device architecture was: ITO/PEDOT:PSS/PBOSPh:PC71BM/Ca/Al. After optimization studies, best results for 130 nm thickness, Polymer:PC71BM with 1:2 ratio, V-oc, J(sc), FF, PCE (%) were found as 0.62 V, 4.53 mA cm(-2), 0.58, 1.63% under illumination of AM 1.5 G 100 mW cm(-2).


Investigation the effect of π bridge and side chain on photovoltaic properties of benzodithiophene and quinoxaline based conjugated polymers
Taşkaya Aslan, Sultan; Alemdar, Eda; Hacıefendioğlu, Tuğba; UDUM, YASEMİN; Toppare, Levent Kamil; Yıldırım, Erol; Çırpan, Ali (2022-04-15)
© 2022 Elsevier LtdA series of donor–acceptor type alternative polymers containing 2D-BDT and 1D-BDT as the donors and quinoxaline as the acceptor were successfully obtained by Stille coupling reactions. Synthesized polymers containing selenophene and thiophene as π-bridges in their backbones and 2-ethylhexylselenophene and 2-ethylhexylalkoxy side groups on the BDT structure were named as P1, P2, P3 and P4, respectively. Eonsetox and Eonsetred were investigated for P1, P2, P3, and P4, respectively. Onset ox...
Synthesis, characterization and photovoltaic properties of benzo[c][1,2,5]oxadiazole based conjugated polymers for organic solar cells
Karakurt, Oğuzhan; Çırpan, Ali; Günbaş, Emrullah Görkem; Department of Chemistry (2021-1-22)
In this thesis, six conjugated polymers were synthesized by coupling of 2,1,3- benzoxadiazole derivatives with donor groups via Stille polycondensation reactions. Moreover, the effect of molecular weight for P1 and P2, effect of position of alkyl chain for P5 and effect of π-bridge groups for P6 which are selenophene and thiophene on optical, electrochemical, and photovoltaic properties were investigated. Also, modifications on alkyl chains of P3 and P4 were performed to increase their functionalities via p...
Synthesis and electro-optical properties of new conjugated hybrid polymers based on furan and fluorene units
Gunes, Arzu; CİHANER, ATİLLA; Önal, Ahmet Muhtar (2013-02-01)
A novel series of hybrid monomers containing furan and fluorene units, namely 2-(2-(furan-2-yl)-9H-fluoren-7-yl)furan (FFF), 2,7-di(furan-2-yl)-9H-fluoren-9-one (FOF) and 2-(2-(furan-2-yl)-9,9-dihexyl-9H-fluoren-7-yl)furan (FHF), was synthesized and their electrochemical polymerization was achieved via potential cycling. Optical and electrochemical properties of the polymers, poly(2-(2-(furan-2-yl)9H-fluoren-7-yl)furan (PFFF), poly(2,7-di(furan-2-yl)-9H-fluoren-9-one) (PFOF) and poly(2-(2-(furan2-yl)-9,9-di...
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...
The impact of [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole structure on the optoelectronic properties of conjugated polymers
Alkan, Ecem Aydan; GÖKER, SEZA; Sarigul, Hatice; Yıldırım, Erol; Udum, Yasemin Arslan; Toppare, Levent Kamil (2020-04-01)
Two novel conjugated near-infrared (NIR) absorbing donor-acceptor type copolymers comprising benzodithiophene as the donor and [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole derivatives as the acceptors, spaced with thiophene as the pi-bridge, were designed and synthesized via Stille polycondensation reaction. The effect of acceptor strength on optoelectronic properties was targeted and investigated. Branched alkyl chains (the extended 2-octyl-1-dodecyl alkyl chain; -C8C12) were introduced to 5H-[1,2,3]t...
Citation Formats
S. GÖKER, G. Hizalan, S. O. Hacioglu, and L. K. Toppare, “Investigation of Optical and Electrochemical Properties of Benzene Based Solution Processable 2,1,3-Benzooxadiazole Comprising Polymers,” JOURNAL OF THE ELECTROCHEMICAL SOCIETY, pp. 0–0, 2020, Accessed: 00, 2020. [Online]. Available: