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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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

Micael Paulino¹, Ignacio Pérez-Juste², María Magdalena Cid²

¹Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516Caparica, Portugal.

The Journal of Organic Chemistry

|October 15, 2022

Summary

This study introduces a pH- and light-responsive 2-hydroxychalcone-β-cyclodextrin conjugate, a novel supramolecular receptor. Its properties can be tuned by pH and light, enabling controlled self-assembly for functional materials.

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Area of Science:

Supramolecular Chemistry
Materials Science
Organic Chemistry

Background:

Stimuli-responsive supramolecular receptors are key for creating self-assembled functional materials.
Chalcone-based photoswitches offer dynamic molecular behavior.
β-cyclodextrin hosts provide versatile platforms for molecular recognition.

Purpose of the Study:

To design and synthesize a novel pH- and light-responsive 2-hydroxychalcone-β-cyclodextrin conjugate.
To characterize the conjugate's photochemical and supramolecular properties.
To investigate the influence of pH and light on its self-inclusion complexation behavior.

Main Methods:

Synthesis of the 2-hydroxychalcone-β-cyclodextrin conjugate.
Spectroscopic characterization techniques (e.g., NMR, UV-Vis).
Computational modeling to understand structural and binding properties.

Main Results:

The conjugate (1-Ct) exhibits reversible photochemical transformations between trans-chalcone, cis-chalcone/hemiketal, and flavylium cation forms depending on pH and light.
Intramolecular self-inclusion complexation constants were determined for different forms: K_intra = 14 for 1-Ct, K_intra = 3 for 1-AH+, and K_intra = 179 for 1-Cc/1-B.
The stability and binding properties of the supramolecular complexes can be precisely controlled by manipulating pH and light stimuli.

Conclusions:

A novel stimuli-responsive supramolecular receptor based on a 2-hydroxychalcone-β-cyclodextrin conjugate was successfully synthesized and characterized.
The conjugate demonstrates tunable self-inclusion complexation behavior modulated by pH and light, offering a mechanism for controlled molecular assembly.
This work provides a foundation for developing advanced self-assembled functional materials with switchable properties for diverse applications.