Evaluation
of Hydrogen-Bond Acceptors for Redox-Switchable
Resorcin[4]arene Cavitands
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Abstract
Various H-bond acceptor groups were
evaluated for their propensity
to induce conformational switching between the kite and vase forms
of diquinone-diquinoxaline resorcin[4]arene cavitands upon redox interconversion.
The H-bond acceptors were placed on the quinoxaline walls with the
purpose of stabilizing the vase form only in the reduced hydroquinone
state of the cavitand by forming H-bonds with the hydroquinone OH
groups. Design guidelines for successful acceptors were derived. The
carboxamide acceptor was shown to be the best candidate. Based on
this moiety, a redox-switchable triptycene-based basket that can completely
sterically encapsulate a guest in its closed vase conformation was
prepared. The basket binds small molecule guests with association
constants of up to 10<sup>4</sup> M<sup>–1</sup> in mesitylene-<i>d</i><sub>12</sub> and exhibits slow guest exchange kinetics
with a half-life for guest release in the order of 10<sup>4</sup> s