Binding of flavylium ions to sulfonatocalix[4]arene and implication in the photorelease of biologically relevant guests in water

Miguel A. Romero, Pedro Mateus, Beatriz Matos, Ángel Acunã, Luis Garciá-Rió, Jesús F. Arteaga, Uwe Pischel, Nuno Basílio

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The formation of host-guest complexes between seven flavylium cations and water-soluble p-sulfonatocalix[4]arene (SC4) was investigated by UV/vis absorption, fluorescence, and NMR spectroscopies. The results show the cationic guests form complexes with affinities in the submillimolar range. A representative chalcone/flavylium photoswitch was investigated in more detail regarding its pH- A nd light-triggered interconversion between the two forms. The dramatic affinity differentiation of the SC4 binding of the two switchable species (40 M-1 for the trans-chalcone versus 3.5 × 104 M-1 for the flavylium cation) enables the pH-gated photocontrol of the complexation process. These responsive properties were explored to demonstrate the competitive and selective release of biologically relevant guests from their supramolecular complexes with p-sulfonatocalix[4]arene (SC4), following the principle of AND logic. The guest release can be reverted by the thermally activated reaction of the flavylium ion back to the trans-chalcone.

Original languageEnglish
Pages (from-to)10852-10859
Number of pages8
JournalJournal of Organic Chemistry
Volume84
Issue number17
DOIs
Publication statusPublished - 6 Sep 2019

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