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Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media
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...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9821991/ https://www.ncbi.nlm.nih.gov/pubmed/36615457 http://dx.doi.org/10.3390/molecules28010261 |
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author | Burilov, Vladimir Fatykhova, Aigul Mironova, Diana Sultanova, Elza Nugmanov, Ramil Artemenko, Alina Volodina, Anastasia Daminova, Amina Evtugyn, Vladimir Solovieva, Svetlana Antipin, Igor |
author_facet | Burilov, Vladimir Fatykhova, Aigul Mironova, Diana Sultanova, Elza Nugmanov, Ramil Artemenko, Alina Volodina, Anastasia Daminova, Amina Evtugyn, Vladimir Solovieva, Svetlana Antipin, Igor |
author_sort | Burilov, Vladimir |
collection | PubMed |
description | 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 (NEt(3), DABCO and iPr(2)EtN), 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. |
format | Online Article Text |
id | pubmed-9821991 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-98219912023-01-07 Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media Burilov, Vladimir Fatykhova, Aigul Mironova, Diana Sultanova, Elza Nugmanov, Ramil Artemenko, Alina Volodina, Anastasia Daminova, Amina Evtugyn, Vladimir Solovieva, Svetlana Antipin, Igor Molecules Article 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 (NEt(3), DABCO and iPr(2)EtN), 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. MDPI 2022-12-28 /pmc/articles/PMC9821991/ /pubmed/36615457 http://dx.doi.org/10.3390/molecules28010261 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Burilov, Vladimir Fatykhova, Aigul Mironova, Diana Sultanova, Elza Nugmanov, Ramil Artemenko, Alina Volodina, Anastasia Daminova, Amina Evtugyn, Vladimir Solovieva, Svetlana Antipin, Igor Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media |
title | Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media |
title_full | Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media |
title_fullStr | Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media |
title_full_unstemmed | Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media |
title_short | Oxyethylated Fluoresceine—(thia)calix[4]arene Conjugates: Synthesis and Visible-Light Photoredox Catalysis in Water–Organic Media |
title_sort | oxyethylated fluoresceine—(thia)calix[4]arene conjugates: synthesis and visible-light photoredox catalysis in water–organic media |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9821991/ https://www.ncbi.nlm.nih.gov/pubmed/36615457 http://dx.doi.org/10.3390/molecules28010261 |
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