A rigid C3v-symmetrical host for saccharide recognition: 1,3,5-tris(2-hydroxyaryl)-2,4,6-trimethylbenzenes.
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.
Abe
Hajime
H
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama, 930-0194 Japan.
Aoyagi
Yoshinobu
Y
Inouye
Masahiko
M
D001555:Benzene Derivatives / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy
D001555:Benzene Derivatives; D002241:Carbohydrates