1. Singlet Oxygen Responsive Molecular Receptor to Modulate Atropisomerism and Cation Binding.
- Author
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Bouteille, Quentin, Sonet, Dorian, Hennebelle, Marc, Desvergne, Jean‐Pierre, Morvan, Estelle, Scalabre, Antoine, Pouget, Emilie, Méreau, Raphaël, and Bibal, Brigitte
- Subjects
REACTIVE oxygen species ,ANTHRACENE derivatives ,BINDING constant ,CYCLOELIMINATION reactions ,CATIONS ,MODULAR design ,ANTHRACENE ,MOLECULAR recognition - Abstract
In switchable molecular recognition, 1O2 stimulus responsive receptors offer a unique structural change that is rarely exploited. The employed [4+2] reaction between 1O2 and anthracene derivatives is quantitative, reversible and easily implemented. To evaluate the full potential of this new stimulus, a non‐macrocyclic anthracene‐based host was designed for the modular binding of cations. The structural investigation showed that 1O2 controlled the atropisomerism in an on/off fashion within the pair of hosts. The binding studies revealed higher association constants for the endoperoxide receptor compared to the parent anthracene, due to a more favoured preorganization of the recognition site. The fatigue of the 1O2 switchable hosts and their complexes was monitored over five cycles of cycloaddition/cycloreversion. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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