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Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes

A series of fluorescent calix[4]arene scaffolds bearing electron-rich carbazole moiety conjugated at the lower rim have been prepared. Studies of the fluorescence quenching in the presence of the N-methyl pyridinium guest revealed that the electronic properties of the distal phenolic ring play a maj...

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Autores principales: Rawat, Varun, Vigalok, Arkadi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457996/
https://www.ncbi.nlm.nih.gov/pubmed/36080456
http://dx.doi.org/10.3390/molecules27175689
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author Rawat, Varun
Vigalok, Arkadi
author_facet Rawat, Varun
Vigalok, Arkadi
author_sort Rawat, Varun
collection PubMed
description A series of fluorescent calix[4]arene scaffolds bearing electron-rich carbazole moiety conjugated at the lower rim have been prepared. Studies of the fluorescence quenching in the presence of the N-methyl pyridinium guest revealed that the electronic properties of the distal phenolic ring play a major role in the host–guest complexation. In particular, placing an electron-donating piperidine fragment at that ring significantly increased the host–guest interactions, while introducing the same fragment into the proximal phenolic ring weakened the fluorescence response. These results suggest that the dominant interactions between the guest and calixarene cavity involve the oxygen-depleted fluorophore-bearing aromatic ring and not the more electron-rich unsubstituted phenolic fragments.
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spelling pubmed-94579962022-09-09 Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes Rawat, Varun Vigalok, Arkadi Molecules Article A series of fluorescent calix[4]arene scaffolds bearing electron-rich carbazole moiety conjugated at the lower rim have been prepared. Studies of the fluorescence quenching in the presence of the N-methyl pyridinium guest revealed that the electronic properties of the distal phenolic ring play a major role in the host–guest complexation. In particular, placing an electron-donating piperidine fragment at that ring significantly increased the host–guest interactions, while introducing the same fragment into the proximal phenolic ring weakened the fluorescence response. These results suggest that the dominant interactions between the guest and calixarene cavity involve the oxygen-depleted fluorophore-bearing aromatic ring and not the more electron-rich unsubstituted phenolic fragments. MDPI 2022-09-03 /pmc/articles/PMC9457996/ /pubmed/36080456 http://dx.doi.org/10.3390/molecules27175689 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
Rawat, Varun
Vigalok, Arkadi
Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes
title Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes
title_full Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes
title_fullStr Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes
title_full_unstemmed Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes
title_short Electronic Tuning of Host-Guest Interactions within the Cavities of Fluorophore-Appended Calix[4]arenes
title_sort electronic tuning of host-guest interactions within the cavities of fluorophore-appended calix[4]arenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457996/
https://www.ncbi.nlm.nih.gov/pubmed/36080456
http://dx.doi.org/10.3390/molecules27175689
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