Quantitative Kinetic Modeling in Photoresponsive Supramolecular Chemistry: The Case of Water-Soluble Azobenzene/Cyclodextrin Complexes

J Org Chem. 2020 May 15;85(10):6509-6518. doi: 10.1021/acs.joc.0c00461. Epub 2020 May 5.

Abstract

Hydrophilic host-guest complexes, consisting of water-soluble azobenzene and α-, β-, or γ-cyclodextrins, have been proposed as a model to study supramolecular photoresponsive systems in aqueous environments through a full spectrometric approach combined with a simulation and data fitting methodology. Various essential and complementary spectroscopic techniques have been used: circular dichroism to determine whether the complex is formed or not, NMR for the stoichiometry elucidation, and UV-visible spectrophotometry to obtain the association equilibrium constant of each complex and the quantum yield for each photochemical process. A step-by-step fitting procedure is presented, which enables the determination of all thermodynamic and photokinetic parameters. A sequential methodology is applied to dissipate all uncertainties on the variability of the results and to develop a relevant and reliable protocol applicable to other types of complexes. The proposed procedure has thus been shown to be very robust and largely applicable to other photoresponsive host-guest systems.

Publication types

  • Research Support, Non-U.S. Gov't