Chiral Molecular Arrangement Behaviour of Unsymmetrical Sugar-Based Gelators by Introduction of Steroisomeric Alanine Moiety

Abstract

We have newly synthesized unsymmetrical D-sugar-based hydrogelators, which have either D-alanine (1) or L-alanine (2) moieties and their chiral molecular arrangements were characterized by TEM, powder-XRD, CD and FT-IR spectroscope. The D-sugar-based hydrogelator, which contained D-alanine, showed remarkably slow chiral molecular packing by intermolecular hydrogen bonding interaction in gel formation. Hydrogelator 1 possesses the orthorhombic perpendicular (O-perpendicular to) subcell type according to the wide-angle region of the XRD pattern and the CH2 scissoring band delta(CH2) in the IR spectrum. On the other hand, hydrogel 2, which contained the D-sugar, but L-alanine, did not undergo the chiral molecular arrangement.