Open Access
Molecules, volume 27, issue 13, pages 4197
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
Gudim Nikita S
1
,
Knyazeva Ekaterina A
1, 2
,
Mikhalchenko Ludmila V.
1
,
Mikhailov Maksim S
2
,
Zhang Lu
3
,
Robertson Neil
3
,
Publication type: Journal Article
Publication date: 2022-06-29
PubMed ID:
35807443
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
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%).
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
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Gudim N. S. et al. 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. Vol. 27. No. 13. p. 4197.
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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. Vol. 27. No. 13. p. 4197.
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TY - JOUR
DO - 10.3390/molecules27134197
UR - https://doi.org/10.3390%2Fmolecules27134197
TI - 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
T2 - Molecules
AU - Gudim, Nikita S
AU - Mikhalchenko, Ludmila V.
AU - Mikhailov, Maksim S
AU - Zhang, Lu
AU - Robertson, Neil
AU - Knyazeva, Ekaterina A
AU - Rakitin, Oleg A.
PY - 2022
DA - 2022/06/29 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 4197
IS - 13
VL - 27
PMID - 35807443
SN - 1420-3049
ER -
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@article{2022_Gudim,
author = {Nikita S Gudim and Ludmila V. Mikhalchenko and Maksim S Mikhailov and Lu Zhang and Neil Robertson and Ekaterina A Knyazeva and Oleg A. Rakitin},
title = {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},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {jun},
url = {https://doi.org/10.3390%2Fmolecules27134197},
number = {13},
pages = {4197},
doi = {10.3390/molecules27134197}
}
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Gudim, Nikita S., et al. “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, vol. 27, no. 13, Jun. 2022, p. 4197. https://doi.org/10.3390%2Fmolecules27134197.