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
Sarigul, Hatice
Yıldırım, Erol
Udum, Yasemin Arslan
Toppare, Levent Kamil
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]triazolo[4 ',5 ':4,5]benzo[1,2-c][1,2,5]thiadiazole and 5H-[1,2,3]triazolo[4 ',5 ':4,5]benzo[1,2-c][1,2,5]selenadiazole for enhanced solubility of polymers which ease the processability hence device constructions. The strongly electron-withdrawing units lead to a substantial change in the absorption properties via promotion of the intramolecular charge transfer band alongside the pi-pi* transition. The resultant soluble polymers were characterized via cyclic voltammetry to determine highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels as -5.00 and -3.92 eV for PSBT and -4.86 and -4.04 eV for PSeBT, respectively. Electronic band gaps of the copolymers were calculated as 1.08 eV for PSBT and 0.82 eV for PSeBT, respectively. NIR absorbing copolymers were used to construct electrochromic devices.


Synthesis of bistriphenylamine- and benzodithiophene-based random conjugated polymers for organic photovoltaic applications
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)...
Dikbıyık, Dilan Ece; Çırpan, Ali; Hızalan Özsoy, Gönül; Department of Chemistry (2022-1-28)
In this study, a series of the Donor -π bridge- Acceptor type conjugated polymers (PT1, PT2, and PT3) were designed and synthesized via Pd-catalyzed Stille polycondensation reactions. Synthesized polymers were used as donor moieties and blended with acceptor unit PC71BM to form the active layer of the bulk heterojunction organic solar cell (BHJ OSC). Polymers contain electron-deficient benzothiadiazole (BT) as acceptor unit and electron-rich benzodithiophene (BDT) as donor unit. Moreover, thiophene [T], sel...
Influence of hydrogen bonding on electrochromic properties of conducting polymers
Akpinar, Hava; Nurioglu, Ayda Goycek; Toppare, Levent Kamil (2012-09-01)
4,7-Bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-phenyl-1H-benzo[d]imidazole (BImBEd) was synthesized via Stille coupling reaction of 4,7-dibromo-2-phenyl-1H-benzo[d]imidazole (BImB) with monostannylated 3,4-ethylenedioxythiophene (EDOT). In order to figure out the presence of an intramolecular hydrogen bonding between the amine bond of the imidazole ring and the oxygen of the EDOT molecule, different amounts of trifluoroacetic acid (TFA) and concentrated sodium hydroxide (NaOH) solutions were added duri...
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...
Citation Formats
E. A. Alkan, S. GÖKER, H. Sarigul, E. Yıldırım, Y. A. Udum, and L. K. Toppare, “The impact of [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole structure on the optoelectronic properties of conjugated polymers,” JOURNAL OF POLYMER SCIENCE, pp. 956–968, 2020, Accessed: 00, 2020. [Online]. Available: