BOUTEILLE, Quentin; SONET, Dorian; HENNEBELLE, Marc; DESVERGNE, Jean‐pierre; MORVAN, Estelle; SCALABRE, Antoine; POUGET, Emilie; MEREAU, Raphael; BIBAL, Brigitte

doi:10.1002/chem.202203210

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BOUTEILLE, Quentin

Institut des Sciences Moléculaires [ISM]

SONET, Dorian

HENNEBELLE, Marc

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Chemistry - A European Journal. 2023-01-13, vol. 29, n° 12, p. e202203210

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In switchable molecular recognition, 1 O 2 stimulus responsive receptors offer a unique structural change that is rarely exploited. The employed [4+2] reaction between 1 O 2 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 1 O 2 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 1 O 2 switchable hosts and their complexes was monitored over five cycles of cycloaddition/cycloreversion.< Leer menos

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Singlet Oxygen Responsive Molecular Receptor to Modulate Atropisomerism and Cation Binding

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