Journal of Organic Chemistry, volume 85, issue 14, pages 9255-9263
Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution
1
Faculty of Natural Sciences, Technische Universität Chemnitz, 09107 Chemnitz, Germany
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3
Department of Chemistry and Pharmacy, University Erlangen−Nürnberg, Nikolaus-Fiebiger-Str. 10, 91058 Erlangen, Germany
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Publication type: Journal Article
Publication date: 2020-06-25
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Control of a receptor isomerization bearing multiple light-switchable subunits in a confined space is critical for the design of synthetic molecular machines. Towards this goal, a new azacryptand containing three azobenzene subunits has been developed and its photoisomerization in aqueous solution has been studied depending on anion coordination and recognition by a larger host - cucurbit[8]uril. The cryptand in its hexaprotonated form shows considerable affinity for fluoride and perchlorate, which in turn affects the isomer distribution of the receptor under UV-light irradiations stabilizing isomers of the cryptand with Z-configurations. Cucurbit[8]uril (CB[8]) was found to be able to encapsulate isomers of the cryptand by forming a Matryoshka-type complex . The irradiation of a 10:1 CB[8] - cryptand mixture has led to a selective conversion of the cryptand to the E,E,Z isomer inside CB[8]. It has been demonstrated that the addition of fluoride to the resulted complex induces a release of the cryptand as a major E,E,E isomer, while other studied anions were ineffective in this reaction. To our knowledge, this work presents a first example of a host-controlled photoisomerization of an anion receptor bearing multiple switching azobenzenes and model the function of naturally occurring chaperones.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Oshchepkov A. S. et al. Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 9255-9263.
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Oshchepkov A. S., Namashivaya S. S. R., Khrustalev V. N., Hampel F. R., Laikov D., Kataev E. Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 9255-9263.
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TY - JOUR
DO - 10.1021/acs.joc.0c01260
UR - https://doi.org/10.1021%2Facs.joc.0c01260
TI - Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution
T2 - Journal of Organic Chemistry
AU - Namashivaya, Siva S R
AU - Khrustalev, Victor N.
AU - Laikov, Dimitri
AU - Kataev, Evgeny
AU - Oshchepkov, Aleksandr S.
AU - Hampel, Frank R.
PY - 2020
DA - 2020/06/25 00:00:00
PB - American Chemical Society (ACS)
SP - 9255-9263
IS - 14
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2020_Oshchepkov,
author = {Siva S R Namashivaya and Victor N. Khrustalev and Dimitri Laikov and Evgeny Kataev and Aleksandr S. Oshchepkov and Frank R. Hampel},
title = {Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021%2Facs.joc.0c01260},
number = {14},
pages = {9255--9263},
doi = {10.1021/acs.joc.0c01260}
}
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MLA
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Oshchepkov, Aleksandr S., et al. “Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution.” Journal of Organic Chemistry, vol. 85, no. 14, Jun. 2020, pp. 9255-9263. https://doi.org/10.1021%2Facs.joc.0c01260.