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

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

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)14422-14432
Number of pages11
JournalJournal of Organic Chemistry
Volume87
Issue number21
DOIs
Publication statusPublished - 4 Nov 2022

Keywords

  • Binding energy
  • Functional materials
  • pH
  • Binding properties
  • Building blockes
  • Chalcones
  • Flavylium
  • Hemiketals
  • Light irradiations
  • Photo-responsive
  • Photoswitch
  • Reaction network
  • Stimuli-responsive
  • Cyclodextrins

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