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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

Procedencia

Ficha

Título:: 2-Hydroxychalcone−β-cyclodextrin conjugate with pH-modulated photoresponsive binding properties
Tema:: 2307 Química Física
Descrición:: 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/Produtor:: Paulino, Micael; Perez Juste, Ignacio; Cid Fernández, María Magdalena; Da Silva, José P.; Pereira, M. Manuela A.; Basílio, Nuno
Editor:: The Journal of Organic Chemistry; Química Física; Química orgánica; Química Cuántica; Síntese, Estructura e Simulación (S3)
Dereitos:: Attribution 4.0 International; © 2022 American Chemical Society; https://creativecommons.org/licenses/by/4.0/; openAccess
Data:: 2024-01-24T12:31:30Z; 2022-11-04; 2024-01-22T13:52:58Z
Tipo de recurso:: article

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        < mods:namePart > Da Silva, José P. </ mods:namePart >
        
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        < mods:namePart > Pereira, M. Manuela A. </ mods:namePart >
        
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        < mods:namePart > Basílio, Nuno </ mods:namePart >
        
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        < mods:dateAccessioned encoding =" iso8601 " > 2024-01-24T12:31:30Z </ mods:dateAccessioned >
        
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        < mods:dateIssued encoding =" iso8601 " > 2022-11-04 </ mods:dateIssued >
        
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        < mods:identifier type =" citation " > The Journal of Organic Chemistry, 87(21): 14422-14432 (2022) </ mods:identifier >
        
        < mods:identifier type =" issn " > 0022326315206904 </ mods:identifier >
        
        < mods:identifier type =" uri " > http://hdl.handle.net/11093/5790 </ mods:identifier >
        
        < mods:identifier type =" doi " > 10.1021/acs.joc.2c01875 </ mods:identifier >
        
        < mods:identifier type =" editor " > https://doi.org/10.1021/acs.joc.2c01875 </ mods:identifier >
        
        < 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:languageTerm authority =" rfc3066 " > eng </ mods:languageTerm >
        
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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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