KFU. Card publication. Oxyethylated fluoresceine—(thia)calix[4]arene conjugates: synthesis and visible-light photoredox catalysis in water

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OXYETHYLATED FLUORESCEINE&MDASH;(THIA)CALIX[4]ARENE CONJUGATES: SYNTHESIS AND VISIBLE-LIGHT PHOTOREDOX CATALYSIS IN WATER&NDASH;ORGANIC MEDIA

Form of presentation

Articles in international journals and collections

Year of publication

2023

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Authors, employees of KFU

Daminova Amina Galeevna, author

Bibliographic description in the original language

Burilov V., Fatykhova A., Mironova D., Sultanova E., Nugmanov R., Artemenko A., Volodina A., Daminova A., Evtugyn V., Solovieva S., Antipin I. Oxyethylated fluoresceine—(thia)calix[4]arene conjugates: synthesis and visible-light photoredox catalysis in water–organic media / V. Burilov, A. Fatykhova, D. Mironova, E. Sultanova, R. Nugmanov, A. Artemenko, A. Volodina, A. Daminova, V .Evtugyn, S. Solovieva, I. Antipin // Molecules. - 2023. - V. 28. - � 261. - P. 1-18.

Annotation

Fluorescent derivatives attract the attention of researchers for their use as sensors, photocatalysts and for the creation of functional materials. In order to create amphiphilic fluorescent derivatives of calixarenes, a fluorescein derivative containing oligoethylene glycol and propargyl groups was obtained. The resulting fluorescein derivative was introduced into three different (thia)calix[4]arene azide derivatives. For all synthesized compounds, the luminescence quantum yields have been established in different solvents. Using UV-visible spectroscopy, dynamic light scattering, as well as transmission and confocal microscopy, aggregation of macrocycles was studied. It was evaluated that calixarene derivatives with alkyl substituents form spherical aggregates, while symmetrical tetrafluorescein-containing thiacalix[4]arene forms extended worm-like aggregates. The macrocycle containing tetradecyl fragments was found to be the most efficient in photoredox ipso-oxidation of phenylboronic acid. In addition, it was shown that in a number of different electron donors (NEt3, DABCO and iPr2EtN), the photoredox ipso-oxidation proceeds best with triethylamine. It has been shown that a low molecular weight surfactant Triton-X100 can also improve the photocatalytic abilities of an oligoethylene glycol fluorescein derivative, thus showing the importance of a combination of micellar and photoredox catalysis.

Keywords

calixarene, thiacalixarene, fluorescein, luminescence, click chemistry, photoredox catalysis

The name of the journal

Molecules

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=310643&p_lang=2

Resource files

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F_molecules_28_00261_v2.pdf	6,00	pdf	show / download

Full metadata record

Field DC	Value	Language
dc.contributor.author	Daminova Amina Galeevna	ru_RU
dc.date.accessioned	2023-01-01T00:00:00Z	ru_RU
dc.date.available	2023-01-01T00:00:00Z	ru_RU
dc.date.issued	2023	ru_RU
dc.identifier.citation	Burilov V., Fatykhova A., Mironova D., Sultanova E., Nugmanov R., Artemenko A., Volodina A., Daminova A., Evtugyn V., Solovieva S., Antipin I. Oxyethylated fluoresceine—(thia)calix[4]arene conjugates: synthesis and visible-light photoredox catalysis in water–organic media / V. Burilov, A. Fatykhova, D. Mironova, E. Sultanova, R. Nugmanov, A. Artemenko, A. Volodina, A. Daminova, V .Evtugyn, S. Solovieva, I. Antipin // Molecules. - 2023. - V. 28. - � 261. - P. 1-18.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=310643&p_lang=2	ru_RU
dc.description.abstract	Molecules	ru_RU
dc.description.abstract	Fluorescent derivatives attract the attention of researchers for their use as sensors, photocatalysts and for the creation of functional materials. In order to create amphiphilic fluorescent derivatives of calixarenes, a fluorescein derivative containing oligoethylene glycol and propargyl groups was obtained. The resulting fluorescein derivative was introduced into three different (thia)calix[4]arene azide derivatives. For all synthesized compounds, the luminescence quantum yields have been established in different solvents. Using UV-visible spectroscopy, dynamic light scattering, as well as transmission and confocal microscopy, aggregation of macrocycles was studied. It was evaluated that calixarene derivatives with alkyl substituents form spherical aggregates, while symmetrical tetrafluorescein-containing thiacalix[4]arene forms extended worm-like aggregates. The macrocycle containing tetradecyl fragments was found to be the most efficient in photoredox ipso-oxidation of phenylboronic acid. In addition, it was shown that in a number of different electron donors (NEt3, DABCO and iPr2EtN), the photoredox ipso-oxidation proceeds best with triethylamine. It has been shown that a low molecular weight surfactant Triton-X100 can also improve the photocatalytic abilities of an oligoethylene glycol fluorescein derivative, thus showing the importance of a combination of micellar and photoredox catalysis.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	calixarene	ru_RU
dc.subject	thiacalixarene	ru_RU
dc.subject	fluorescein	ru_RU
dc.subject	luminescence	ru_RU
dc.subject	click chemistry	ru_RU
dc.subject	photoredox catalysis	ru_RU
dc.title	Oxyethylated fluoresceine—(thia)calix[4]arene conjugates: synthesis and visible-light photoredox catalysis in water–organic media	ru_RU
dc.type	Articles in international journals and collections	ru_RU