Hybrid cavitand capsule with hydrogen bonds and metal-ligand coordination bonds: guest encapsulation with anion assistance.
Multifunctionalized C(2v)-cavitand 1 was synthesized in six steps from a tetrabromo cavitand. A 1:1 mixture of 1 and 2 in CDCl(3) or CD(2)Cl(2) quantitatively self-assemble into a supramolecular hybrid capsule 3 through hydrogen bond and metal-ligand coordination bond. The cavity of the capsule 3 is filled with triflate ion and penetrated alkyl groups of ureides. Capsule 3 encapsulates a neutral guest molecule such as 4,4'-diiodobiphenyl (4) with the assistance of an anion. The encapsulation complex was identified by an NMR technique. The kinetics of guest exchange is controllable by the amounts and/or types of anions or other influences such as the polarity of the solvent.
Yamanaka
Masamichi
M
Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan. smyaman@ipc.shizuoka.ac.jp
Toyoda
Naoaki
N
Kobayashi
Kenji
K
D000838:Anions / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D006860:Hydrogen Bonding; D007700:Kinetics; D008024:Ligands; D008968:Molecular Conformation; D009944:Organoplatinum Compounds / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry*; D013237:Stereoisomerism
D000838:Anions; D004988:Ethers, Cyclic; D008024:Ligands; D009944:Organoplatinum Compounds; D012118:Resorcinols; C442939:cavitand