Light-Driven Photoconversion of Squaramides with Implications in Anion Transport

[Image: see text] Simple, clean and fast photoconversion of aniline-derived squaramides was achieved by flashlight illumination. UV irradiation enabled the photochemical squaramide ring-opening to generate 1,2-bisketenes, which DMSO trapped as the nucleophilic oxidant. The only photoproducts isolate...

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Autores principales: Vega, Manel, Martínez-Crespo, Luis, Barceló-Oliver, Miguel, Rotger, Carmen, Costa, Antonio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10204084/
https://www.ncbi.nlm.nih.gov/pubmed/37158572
http://dx.doi.org/10.1021/acs.orglett.3c00993
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author Vega, Manel
Martínez-Crespo, Luis
Barceló-Oliver, Miguel
Rotger, Carmen
Costa, Antonio
author_facet Vega, Manel
Martínez-Crespo, Luis
Barceló-Oliver, Miguel
Rotger, Carmen
Costa, Antonio
author_sort Vega, Manel
collection PubMed
description [Image: see text] Simple, clean and fast photoconversion of aniline-derived squaramides was achieved by flashlight illumination. UV irradiation enabled the photochemical squaramide ring-opening to generate 1,2-bisketenes, which DMSO trapped as the nucleophilic oxidant. The only photoproducts isolated were 3,4-arylamino maleic anhydrides, which present conformational preferences very different from those of their parent squaramides. Similar photoconversion was achieved in MeOH. The UV-mediated time-dependent anion transport inhibition was demonstrated, establishing a new approach for modulating the transport abilities of AD-squaramides.
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spelling pubmed-102040842023-05-24 Light-Driven Photoconversion of Squaramides with Implications in Anion Transport Vega, Manel Martínez-Crespo, Luis Barceló-Oliver, Miguel Rotger, Carmen Costa, Antonio Org Lett [Image: see text] Simple, clean and fast photoconversion of aniline-derived squaramides was achieved by flashlight illumination. UV irradiation enabled the photochemical squaramide ring-opening to generate 1,2-bisketenes, which DMSO trapped as the nucleophilic oxidant. The only photoproducts isolated were 3,4-arylamino maleic anhydrides, which present conformational preferences very different from those of their parent squaramides. Similar photoconversion was achieved in MeOH. The UV-mediated time-dependent anion transport inhibition was demonstrated, establishing a new approach for modulating the transport abilities of AD-squaramides. American Chemical Society 2023-05-09 /pmc/articles/PMC10204084/ /pubmed/37158572 http://dx.doi.org/10.1021/acs.orglett.3c00993 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 Vega, Manel
Martínez-Crespo, Luis
Barceló-Oliver, Miguel
Rotger, Carmen
Costa, Antonio
Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
title Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
title_full Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
title_fullStr Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
title_full_unstemmed Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
title_short Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
title_sort light-driven photoconversion of squaramides with implications in anion transport
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10204084/
https://www.ncbi.nlm.nih.gov/pubmed/37158572
http://dx.doi.org/10.1021/acs.orglett.3c00993
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AT rotgercarmen lightdrivenphotoconversionofsquaramideswithimplicationsinaniontransport
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