Cargando…

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

[Image: see text] 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 spec...

Descripción completa

Detalles Bibliográficos
Autores principales: Paulino, Micael, Pérez-Juste, Ignacio, Cid, María Magdalena, Da Silva, José P., Pereira, M. Manuela A., Basílio, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9776619/
https://www.ncbi.nlm.nih.gov/pubmed/36242558
http://dx.doi.org/10.1021/acs.joc.2c01875
Descripción
Sumario:[Image: see text] 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.