Semiconducting Alkyl Derivatives of 2,5-Bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole—Effect of the Substituent Position on the Spectroscopic, Electrochemical, and Structural Properties
Тип публикации: Journal Article
Дата публикации: 2013-07-15
scimago Q1
wos Q3
БС1
SJR: 0.914
CiteScore: 6.2
Impact factor: 3.2
ISSN: 19327447, 19327455
Surfaces, Coatings and Films
Electronic, Optical and Magnetic Materials
Physical and Theoretical Chemistry
General Energy
Краткое описание
Unsubstituted 2,5-bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole and four of its derivatives containing solubilizing octyl groups in different positions of the terminal thiophene ring were synthesized (3 new compounds and 2 already reported). Their UV–vis absorption and emission spectra turned out to be strongly dependent on the position of the substituent and showed significant bathochromic shifts of the dominant transition for compounds with the substituents attached to Cα of the terminal ring (λmax > 425 nm). A good correlation was found for the experimentally determined and theoretically calculated excitation energies employing the time-dependent Coulomb-attenuated hybrid exchange-correlation functional using the 6-31G* basis set (TD CAM-B3LYP/6-31G*). The calculations showed, in addition, that the alkyl substituents improved the planarity of the molecule and its aromaticity, and that they raised the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels (the lat...
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Kurach E. et al. Semiconducting Alkyl Derivatives of 2,5-Bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole—Effect of the Substituent Position on the Spectroscopic, Electrochemical, and Structural Properties // Journal of Physical Chemistry C. 2013. Vol. 117. No. 29. pp. 15316-15326.
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Kurach E., Kotwica K., Zapała J., Knor M., Nowakowski R., Djurado D., Toman P., Pfleger J., Zagórska M., Pron A. Semiconducting Alkyl Derivatives of 2,5-Bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole—Effect of the Substituent Position on the Spectroscopic, Electrochemical, and Structural Properties // Journal of Physical Chemistry C. 2013. Vol. 117. No. 29. pp. 15316-15326.
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TY - JOUR
DO - 10.1021/jp4033832
UR - https://doi.org/10.1021/jp4033832
TI - Semiconducting Alkyl Derivatives of 2,5-Bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole—Effect of the Substituent Position on the Spectroscopic, Electrochemical, and Structural Properties
T2 - Journal of Physical Chemistry C
AU - Kurach, Ewa
AU - Kotwica, Kamil
AU - Zapała, Joanna
AU - Knor, Marek
AU - Nowakowski, R
AU - Djurado, David
AU - Toman, Petr
AU - Pfleger, Jiri
AU - Zagórska, Małgorzata
AU - Pron, A.
PY - 2013
DA - 2013/07/15
PB - American Chemical Society (ACS)
SP - 15316-15326
IS - 29
VL - 117
SN - 1932-7447
SN - 1932-7455
ER -
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@article{2013_Kurach,
author = {Ewa Kurach and Kamil Kotwica and Joanna Zapała and Marek Knor and R Nowakowski and David Djurado and Petr Toman and Jiri Pfleger and Małgorzata Zagórska and A. Pron},
title = {Semiconducting Alkyl Derivatives of 2,5-Bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole—Effect of the Substituent Position on the Spectroscopic, Electrochemical, and Structural Properties},
journal = {Journal of Physical Chemistry C},
year = {2013},
volume = {117},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jp4033832},
number = {29},
pages = {15316--15326},
doi = {10.1021/jp4033832}
}
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Kurach, Ewa, et al. “Semiconducting Alkyl Derivatives of 2,5-Bis(2,2′-bithiophene-5-yl)-1,3,4-thiadiazole—Effect of the Substituent Position on the Spectroscopic, Electrochemical, and Structural Properties.” Journal of Physical Chemistry C, vol. 117, no. 29, Jul. 2013, pp. 15316-15326. https://doi.org/10.1021/jp4033832.