D_3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module

(Chemical Equation Presented) A D_3h-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene (3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treated with glycoside, corresponding changes were induced in ¹H NMR, UV, and CD spectra. The titration experiments indicated the participation of not only a 1:1 but also a 1:2 association of a glucosamine derivative guest. Self-association of 3 caused gelation with CDCl₃, and was studied by ¹H NMR and X-ray analysis.