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

Paulino, Micael; Pérez-Juste, Ignacio; Cid, María Magdalena; Da Silva, José Paulo; Pereira, M. Manuela A.; Basílio, Nuno

http://hdl.handle.net/10400.1/18926

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Authors

Pereira, M. Manuela A.

Basílio, Nuno

Abstract(s)

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-beta-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 beta-cyclodextrin host, 1Ct, 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.