1568337-45-0Relevant articles and documents
Evaluation of hydrogen-bond acceptors for redox-switchable resorcin[4]arene cavitands
Pochorovski, Igor,Milic, Jovana,Kolarski, Dusan,Gropp, Cornelius,Schweizer, W. Bernd,Diederich, Francois
, p. 3852 - 3858 (2014)
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 104 M-1 in mesitylene-d12 and exhibits slow guest exchange kinetics with a half-life for guest release in the order of 104 s.