title: A rigid C3v-symmetrical host for saccharide recognition: 1,3,5-tris(2-hydroxyaryl)-2,4,6-trimethylbenzenes.
abstract: A rigid C(3v)-symmetrical host molecule, syn-1,3,5-tris(2-hydroxy-5-pentylphenyl)-2,4,6-trimethylbenzene, was readily obtained via Suzuki coupling and thermal atropisomerization. The host molecule effectively associated with various saccharides by multipoint hydrogen bonds, whereas its anti-atropisomer and analogue lacking in methyl groups showed much weaker association with saccharides. Thermodynamic analyses suggested that the difference of the association strength was caused by entropic factors.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama, 930-0194 Japan.
authors.forename: Hajime
authors.initials: H
authors.lastname: Abe
authors.forename: Yoshinobu
authors.initials: Y
authors.lastname: Aoyagi
authors.forename: Masahiko
authors.initials: M
authors.lastname: Inouye
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy
chemical_list: D001555:Benzene Derivatives; D002241:Carbohydrates