2‑Hydroxychalcone−β-Cyclodextrin Conjugate with pH-Modulated Photoresponsive Binding Properties

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 comp...

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Published inJournal of organic chemistry Vol. 87; no. 21; pp. 14422 - 14432
Main Authors Paulino, Micael, Pérez-Juste, Ignacio, Cid, María Magdalena, Da Silva, José P., Pereira, M. Manuela A., Basílio, Nuno
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.11.2022
Subjects
beta-Cyclodextrins - chemistry
Chalcone - chemistry
Chalcones - chemistry
Hydrogen-Ion Concentration
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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 (K intra = 14) than 1-AH + (K intra = 3) and weaker than 1-Cc/1-B (overall K intra = 179), allowing control over their stability and binding properties by combinations of pH and light stimuli.
AbstractList 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 ( K intra = 14) than 1-AH + ( K intra = 3) and weaker than 1-Cc / 1-B (overall K intra = 179), allowing control over their stability and binding properties by combinations of pH and light stimuli.
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 (K intra = 14) than 1-AH + (K intra = 3) and weaker than 1-Cc/1-B (overall K intra = 179), allowing control over their stability and binding properties by combinations of pH and light stimuli.
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 ( ) and its characterization by spectroscopic and computational methods. follows the typical reaction network of -chalcone-flavylium photoswitches. Upon light irradiation, can be photochemically converted into the -chalcone/hemiketal forms ( / ) under neutral pH conditions or to the flavylium cation ( ) at acidic pH values. This stimuli-responsive β-cyclodextrin host, , was found to form stronger intramolecular self-inclusion complexes ( = 14) than ( = 3) and weaker than / (overall = 179), allowing control over their stability and binding properties by combinations of pH and light stimuli.
Author Cid, María Magdalena
Da Silva, José P.
Paulino, Micael
Basílio, Nuno
Pérez-Juste, Ignacio
Pereira, M. Manuela A.
AuthorAffiliation University of Algarve
Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia
Universidade de Vigo
Facultade de Química, Edificio de Ciencias Experimentais
Centre of Marine Sciences (CCMAR/CIMAR LA)
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Snippet Stimuli-responsive supramolecular receptors are important building blocks for the construction of self-assembled functional materials. We report the design and...
Stimuli-responsive supramolecular receptors are important building blocks for the construction of self-assembled functional materials. We report the design and...
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SubjectTerms beta-Cyclodextrins - chemistry
Chalcone - chemistry
Chalcones - chemistry
Hydrogen-Ion Concentration
Title 2‑Hydroxychalcone−β-Cyclodextrin Conjugate with pH-Modulated Photoresponsive Binding Properties
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