Investigation of Fluorine Atom Effect on Benzothiadiazole Acceptor Unit in Donor Acceptor Donor Systems

Date

2019-07-12

Author

Çakal, Deniz
Akdağ, Akın
Önal, Ahmet Muhtar

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Synthesis of two new pi-conjugated monomers containing fluorine substituted benzothiadiazoles as acceptor units and 3,4-ethylenedioxythiophene (EDOT) as donor unit was accomplished by facilitating Stille cross-coupling reactions (4,7-bis(2,3-dihydrothieno[3,4-b][1,4] dioxin-5-yl)-5-fluorobenzo[c][1,2,5] thiadiazole (E2BTD-F) and 4,7-bis(2,3-dihydrothieno [3,4-b][1,4] dioxin-5-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole (E2BTD-2F)). NMR and HRMS spectra of newly synthesized compounds are in agreement with the structures. To compare fluorine substitution effects, non-fluorinated analogue (4,7-bis(2,3-dihydrothieno[3,4-b][1,4] dioxin-5-yl) benzo[c][1,2,5] thiadiazole (E2BTD)) was also synthesized. Besides a blue shift in their absorption spectra, an anodic shift was also noted in the oxidation potentials of both monomers with fluorine atom substitution on the acceptor unit. This was further confirmed by DFT calculations such that upon fluorine substitution EDOT donor units deviate from planarity. Electropolymerization of the monomers were achieved successfully via potentiodynamic polymerization method. A similar trend in optoelectronic properties was also observed for the polymer films as for the monomers. (C) 2019 The Electrochemical Society.

Subject Keywords

Renewable Energy, Sustainability and the Environment, Electrochemistry, Materials Chemistry, Electronic, Optical and Magnetic Materials, Surfaces, Coatings and Films, Condensed Matter Physics

URI

https://hdl.handle.net/11511/47522

Journal

JOURNAL OF THE ELECTROCHEMICAL SOCIETY

DOI

https://doi.org/10.1149/2.0471912jes

Collections

Department of Chemistry, Article

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Citation Formats

D. Çakal, A. Akdağ, and A. M. Önal, “Investigation of Fluorine Atom Effect on Benzothiadiazole Acceptor Unit in Donor Acceptor Donor Systems,” JOURNAL OF THE ELECTROCHEMICAL SOCIETY, pp. 0–0, 2019, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47522.