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2-Hydroxychalcone−β-cyclodextrin conjugate with pH-modulated photoresponsive binding properties

Identificadores del recurso

The Journal of Organic Chemistry, 87(21): 14422-14432 (2022)

00223263

15206904

http://hdl.handle.net/11093/5790

10.1021/acs.joc.2c01875

https://doi.org/10.1021/acs.joc.2c01875

Origin

File

Title:: 2-Hydroxychalcone−β-cyclodextrin conjugate with pH-modulated photoresponsive binding properties
Tema:: 2307 Química Física
Description:: Stimuli-responsive supramolecular receptors are important building blocks for the construction of self-assembled functional materials. We report the design and synthesis of a pH- and light-responsive 2-hydroxychalcone−β-cyclodextrin conjugate (1-Ct) and its characterization by spectroscopic and computational methods. 1-Ct follows the typical reaction network of trans-chalcone-flavylium photoswitches. Upon light irradiation, 1-Ct can be photochemically converted into the cis-chalcone/hemiketal forms (1-Cc/1-B) under neutral pH conditions or to the flavylium cation (1-AH+) at acidic pH values. This stimuli-responsive β-cyclodextrin host, 1-Ct, was found to form stronger intramolecular self-inclusion complexes (Kintra = 14) than 1-AH+ (Kintra = 3) and weaker than 1-Cc/1-B (overall Kintra = 179), allowing control over their stability and binding properties by combinations of pH and light stimuli.; Fundação para a Ciência e a Tecnologia | Ref. UIDB/50006/2020; Fundação para a Ciência e a Tecnologia| Ref. UIDP/50006/2020; Fundação para a Ciência e a Tecnologia | Ref. UIDB/04326/2020
Idioma:: English
Autor/Productor:: Paulino, Micael; Perez Juste, Ignacio; Cid Fernández, María Magdalena; Da Silva, José P.; Pereira, M. Manuela A.; Basílio, Nuno
Publisher:: The Journal of Organic Chemistry; Química Física; Química orgánica; Química Cuántica; Síntese, Estructura e Simulación (S3)
Rights:: Attribution 4.0 International; © 2022 American Chemical Society; https://creativecommons.org/licenses/by/4.0/; openAccess
Date:: 2024-01-24T12:31:30Z; 2022-11-04; 2024-01-22T13:52:58Z
Tipo de recurso:: article

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        <mods:identifier type="doi">10.1021/acs.joc.2c01875</mods:identifier>
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        <mods:abstract>Stimuli-responsive supramolecular receptors are important building blocks for the construction of self-assembled functional materials. We report the design and synthesis of a pH- and light-responsive 2-hydroxychalcone−β-cyclodextrin conjugate (1-Ct) and its characterization by spectroscopic and computational methods. 1-Ct follows the typical reaction network of trans-chalcone-flavylium photoswitches. Upon light irradiation, 1-Ct can be photochemically converted into the cis-chalcone/hemiketal forms (1-Cc/1-B) under neutral pH conditions or to the flavylium cation (1-AH+) at acidic pH values. This stimuli-responsive β-cyclodextrin host, 1-Ct, was found to form stronger intramolecular self-inclusion complexes (Kintra = 14) than 1-AH+ (Kintra = 3) and weaker than 1-Cc/1-B (overall Kintra = 179), allowing control over their stability and binding properties by combinations of pH and light stimuli.</mods:abstract>
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        <mods:accessCondition type="useAndReproduction">Attribution 4.0 International © 2022 American Chemical Society</mods:accessCondition>
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        <mods:title>2-Hydroxychalcone−β-cyclodextrin conjugate with pH-modulated photoresponsive binding properties</mods:title>
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