The impact of [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole structure on the optoelectronic properties of conjugated polymers

Date

2020-04-01

Author

Alkan, Ecem Aydan
GÖKER, SEZA
Sarigul, Hatice
Yıldırım, Erol
Udum, Yasemin Arslan
Toppare, Levent Kamil

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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.

Subject Keywords

Benzo[1; 2-b; 4; 5-b ']dithiophene, Benzotriazole, Chalcogen, Conjugated polymers, Electrochromism

URI

https://hdl.handle.net/11511/42929

Journal

JOURNAL OF POLYMER SCIENCE

DOI

https://doi.org/10.1002/pol.20190275

Collections

Department of Chemistry, Article

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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: https://hdl.handle.net/11511/42929.