Manipulating stereo-communication in binaphthol-bridged α- and β-cyclodextrins to develop β-selective chiroptical pH switching and anion sensing in water
c
Gennaro
Pescitelli,
c
Valeria
Amendola,
a
Dominique
Armspach
*b
and
Dario
Pasini
*a
Abstract
Molecular structures comprising naturally-occurring, stereodefined cyclodextrins and binaphthyls as bridging units have been realized, designed in such a way that the stereocommunication mode between the two chiral entities is unfavourable (‘chiral mismatch’). The induced strain translates into highly responsive chiroptical behavior. On one side, the binaphthol-containing structure functions as a pH-controlled, single-molecule chiroptical switch, with reversal of the optical activity from acidic to basic conditions in a fully reversible manner. Additionally, the same host molecule demonstrates a pronounced chiroptical response to perrhenate in aqueous solution at pH 2.5, showing excellent selectivity for this specific anion. Computational analysis confirmed that the major effect of ReO4− complexation is making new conformations accessible to the binaphthol moiety with a large variation of the associated dihedral angles.
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