Redox-switchable resorcin[4]arene cavitands: molecular grippers.
Diquinone-based resorcin[4]arene cavitands that open to a kite and close to a vase form upon changing their redox state, thereby releasing and binding guests, have been prepared and studied. The switching mechanism is based on intramolecular H-bonding interactions that stabilize the vase form and are only present in the reduced hydroquinone state. The intramolecular H-bonds were characterized using X-ray, IR, and NMR spectroscopies. Guests were bound in the closed, reduced state and fully released in the open, oxidized state.
Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich, Switzerland.
Igor
I
Pochorovski
Marc-Olivier
MO
Ebert
Jean-Paul
JP
Gisselbrecht
Corinne
C
Boudon
W Bernd
WB
Schweizer
Francois
F
Diederich
D047250:Calixarenes / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D012118:Resorcinols / Q000737:chemistry*
D004988:Ethers, Cyclic; D012118:Resorcinols; C442939:cavitand; C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine