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Article

Novel D-A-π-A1 Type Organic Sensitizers from 4,7-Dibromobenzo[d][1,2,3]thiadiazole and Indoline Donors for Dye-Sensitized Solar Cells

by
Nikita S. Gudim
1,
Ekaterina A. Knyazeva
1,2,
Ludmila V. Mikhalchenko
1,
Maksim S. Mikhailov
2,
Lu Zhang
3,
Neil Robertson
3,* and
Oleg A. Rakitin
1,*
1
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia
2
Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia
3
EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh EH9 3FJ, UK
*
Authors to whom correspondence should be addressed.
Molecules 2022, 27(13), 4197; https://doi.org/10.3390/molecules27134197
Submission received: 27 May 2022 / Revised: 15 June 2022 / Accepted: 27 June 2022 / Published: 29 June 2022
(This article belongs to the Section Organic Chemistry)
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Abstract

Two novel D-A-π-A1 metal-free organic dyes of the KEA series containing benzo[d][1,2,3]thiadiazole (isoBT) internal acceptor, indoline donors fused with cyclopentane or cyclohexane rings (D), a thiophene as a π-spacer, and a cyanoacrylate as an anchor part were synthesized. Monoarylation of 4,7-dibromobenzo[d][1,2,3]thiadiazole by Suzuki-Miyamura cross-coupling reaction showed that in the case of indoline and carbazole donors, the reaction was non-selective, i.e., two monosubstituted derivatives were isolated in each case, whereas only one mono-isomer was formed with phenyl- and 2-thienylboronic acids. This was explained by the fact that heterocyclic indoline and carbazole fragments are much stronger donor groups compared to thiophene and benzene, as confirmed by cyclic voltammetry measurements and calculation of HOMO energies of indoline, carbazole, thiophene and benzene molecules. The structure of monoaryl(hetaryl) derivatives was strictly proven by NMR spectroscopy and X-ray diffraction. The optical and photovoltaic properties observed for the KEA dyes showed that these compounds are promising for the creation of solar cells. A comparison with symmetrical benzo[c][1,2,3]thiadiazole dyes WS-2 and MAX114 showed that the asymmetric nature of benzo[d][1,2,3]thiadiazole KEA dyes leads to a hypsochromic shift of the ICT band in comparison with the corresponding benzo[c][1,2,5]thiadiazole isomers. KEA dyes have a narrow HOMO-LUMO gap of 1.5–1.6 eV. Amongst these dyes, KEA321 recorded the best power efficiency (PCE), i.e., 5.17%, which is superior to the corresponding symmetrical benzo[c][1,2,3]thiadiazole dyes WS-2 and MAX114 (5.07 and 4.90%).
Keywords: benzo[d][1,2,3]thiadiazole; Suzuki cross-coupling reaction; D-A-π-A1 dyes; dye-sensitized solar cells; optical properties; electrochemical properties; power conversion efficiency benzo[d][1,2,3]thiadiazole; Suzuki cross-coupling reaction; D-A-π-A1 dyes; dye-sensitized solar cells; optical properties; electrochemical properties; power conversion efficiency

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MDPI and ACS Style

Gudim, N.S.; Knyazeva, E.A.; Mikhalchenko, L.V.; Mikhailov, M.S.; Zhang, L.; Robertson, N.; Rakitin, O.A. Novel D-A-π-A1 Type Organic Sensitizers from 4,7-Dibromobenzo[d][1,2,3]thiadiazole and Indoline Donors for Dye-Sensitized Solar Cells. Molecules 2022, 27, 4197. https://doi.org/10.3390/molecules27134197

AMA Style

Gudim NS, Knyazeva EA, Mikhalchenko LV, Mikhailov MS, Zhang L, Robertson N, Rakitin OA. Novel D-A-π-A1 Type Organic Sensitizers from 4,7-Dibromobenzo[d][1,2,3]thiadiazole and Indoline Donors for Dye-Sensitized Solar Cells. Molecules. 2022; 27(13):4197. https://doi.org/10.3390/molecules27134197

Chicago/Turabian Style

Gudim, Nikita S., Ekaterina A. Knyazeva, Ludmila V. Mikhalchenko, Maksim S. Mikhailov, Lu Zhang, Neil Robertson, and Oleg A. Rakitin. 2022. "Novel D-A-π-A1 Type Organic Sensitizers from 4,7-Dibromobenzo[d][1,2,3]thiadiazole and Indoline Donors for Dye-Sensitized Solar Cells" Molecules 27, no. 13: 4197. https://doi.org/10.3390/molecules27134197

APA Style

Gudim, N. S., Knyazeva, E. A., Mikhalchenko, L. V., Mikhailov, M. S., Zhang, L., Robertson, N., & Rakitin, O. A. (2022). Novel D-A-π-A1 Type Organic Sensitizers from 4,7-Dibromobenzo[d][1,2,3]thiadiazole and Indoline Donors for Dye-Sensitized Solar Cells. Molecules, 27(13), 4197. https://doi.org/10.3390/molecules27134197

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