Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities

[Image: see text] We report the synthesis of a series of the oxygen-depleted conjugated 5,5′-Bicalix[4]arene compounds bearing various substituents at the terminal positions of the conjugated chain and their fluorescence response to the presence of a cationic N-methylpyridinium guest. The complexati...

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Autores principales: Farber, Michal, Maity, Pintu, Baheti, Abhishek, Golombek, Adina, Schwartz, Tal, Dobrovetsky, Roman, Vigalok, Arkadi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10661034/
https://www.ncbi.nlm.nih.gov/pubmed/37906127
http://dx.doi.org/10.1021/acs.joc.3c01566
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author Farber, Michal
Maity, Pintu
Baheti, Abhishek
Golombek, Adina
Schwartz, Tal
Dobrovetsky, Roman
Vigalok, Arkadi
author_facet Farber, Michal
Maity, Pintu
Baheti, Abhishek
Golombek, Adina
Schwartz, Tal
Dobrovetsky, Roman
Vigalok, Arkadi
author_sort Farber, Michal
collection PubMed
description [Image: see text] We report the synthesis of a series of the oxygen-depleted conjugated 5,5′-Bicalix[4]arene compounds bearing various substituents at the terminal positions of the conjugated chain and their fluorescence response to the presence of a cationic N-methylpyridinium guest. The complexation of this cation within the bicalixarene cavity results in the fluorescence quenching, with the host molecules bearing electron-donating groups demonstrating a stronger fluorescence response. These results show the importance of the electronic effects on the host–guest complexation within the hydrophobic calixarene scaffolds.
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spelling pubmed-106610342023-11-21 Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities Farber, Michal Maity, Pintu Baheti, Abhishek Golombek, Adina Schwartz, Tal Dobrovetsky, Roman Vigalok, Arkadi J Org Chem [Image: see text] We report the synthesis of a series of the oxygen-depleted conjugated 5,5′-Bicalix[4]arene compounds bearing various substituents at the terminal positions of the conjugated chain and their fluorescence response to the presence of a cationic N-methylpyridinium guest. The complexation of this cation within the bicalixarene cavity results in the fluorescence quenching, with the host molecules bearing electron-donating groups demonstrating a stronger fluorescence response. These results show the importance of the electronic effects on the host–guest complexation within the hydrophobic calixarene scaffolds. American Chemical Society 2023-10-31 /pmc/articles/PMC10661034/ /pubmed/37906127 http://dx.doi.org/10.1021/acs.joc.3c01566 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Farber, Michal
Maity, Pintu
Baheti, Abhishek
Golombek, Adina
Schwartz, Tal
Dobrovetsky, Roman
Vigalok, Arkadi
Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities
title Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities
title_full Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities
title_fullStr Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities
title_full_unstemmed Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities
title_short Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities
title_sort long range electronic effects on the host–guest complexation within the oxygen depleted 5,5′-bicalixarene cavities
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10661034/
https://www.ncbi.nlm.nih.gov/pubmed/37906127
http://dx.doi.org/10.1021/acs.joc.3c01566
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