Open Access
Molecules, volume 26, issue 16, pages 4931
Benzothiadiazole vs. Iso-benzothiadiazole: Synthesis, electrochemical and optical properties of d–a–d conjugated molecules based on them
Gudim Nikita S
1
,
Knyazeva Ekaterina A
1, 2
,
Mikhalchenko Ludmila V.
1
,
Golovanov Ivan S
1
,
Popov Vadim V
2
,
Rakitin Oleg A.
1, 2
Publication type: Journal Article
Publication date: 2021-08-14
PubMed ID:
34443520
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
This paper presents an improved synthesis of 4,7-dibromobenzo[d][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[d][1,2,3]thiadiazole (isoBTD) has higher values of ELUMO and energy band gap (Eg), which indicates high electron conductivity, occurring due to the high stability of the molecule in the excited state. We studied the cross-coupling reactions of this dibromide and found that the highest yields of π-spacer–acceptor–π-spacer type compounds were obtained by means of the Stille reaction. Therefore, 6 new structures of this type have been synthesized. A detailed study of the optical and electrochemical properties of the obtained π-spacer–acceptor–π-spacer type compounds in comparison with isomeric structures based on benzo[c][1,2,5]thiadiazole (BTD) showed a red shift of absorption maxima with lower absorptive and luminescent capacity. However, the addition of the 2,2′-bithiophene fragment as a π-spacer resulted in an unexpected increase of the extinction coefficient in the UV/vis spectra along with a blue shift of both absorption maxima for the isoBTD-based compound as compared to the BTD-based compound. Thus, a thorough selection of components in the designing of appropriate compounds with benzo[d][1,2,3]thiadiazole as an internal acceptor can lead to promising photovoltaic materials.
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6 publications, 42.86%
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3 publications, 21.43%
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Gudim N. S. et al. Benzothiadiazole vs. Iso-benzothiadiazole: Synthesis, electrochemical and optical properties of d–a–d conjugated molecules based on them // Molecules. 2021. Vol. 26. No. 16. p. 4931.
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Gudim N. S., Knyazeva E. A., Mikhalchenko L. V., Golovanov I. S., Popov V. V., Obruchnikova N. V., Rakitin O. A. Benzothiadiazole vs. Iso-benzothiadiazole: Synthesis, electrochemical and optical properties of d–a–d conjugated molecules based on them // Molecules. 2021. Vol. 26. No. 16. p. 4931.
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TY - JOUR
DO - 10.3390/molecules26164931
UR - https://doi.org/10.3390%2Fmolecules26164931
TI - Benzothiadiazole vs. Iso-benzothiadiazole: Synthesis, electrochemical and optical properties of d–a–d conjugated molecules based on them
T2 - Molecules
AU - Mikhalchenko, Ludmila V.
AU - Obruchnikova, Natalia V.
AU - Gudim, Nikita S
AU - Knyazeva, Ekaterina A
AU - Popov, Vadim V
AU - Golovanov, Ivan S
AU - Rakitin, Oleg A.
PY - 2021
DA - 2021/08/14 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 4931
IS - 16
VL - 26
PMID - 34443520
SN - 1420-3049
ER -
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@article{2021_Gudim,
author = {Ludmila V. Mikhalchenko and Natalia V. Obruchnikova and Nikita S Gudim and Ekaterina A Knyazeva and Vadim V Popov and Ivan S Golovanov and Oleg A. Rakitin},
title = {Benzothiadiazole vs. Iso-benzothiadiazole: Synthesis, electrochemical and optical properties of d–a–d conjugated molecules based on them},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {aug},
url = {https://doi.org/10.3390%2Fmolecules26164931},
number = {16},
pages = {4931},
doi = {10.3390/molecules26164931}
}
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Gudim, Nikita S., et al. “Benzothiadiazole vs. Iso-benzothiadiazole: Synthesis, electrochemical and optical properties of d–a–d conjugated molecules based on them.” Molecules, vol. 26, no. 16, Aug. 2021, p. 4931. https://doi.org/10.3390%2Fmolecules26164931.