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Org Lett. 2002 May 02;4(9):1423-6. doi: 10.1021/ol025519+.

Molecular design of "super" hydrogelators: understanding the gelation process of azobenzene-based sugar derivatives in water.

Organic letters

Hideki Kobayashi, Arianna Friggeri, Kazuya Koumoto, Masato Amaike, Seiji Shinkai, David N Reinhoudt

Affiliations

  1. Chemotransfiguration Project, Japan Science and Technology Corporation, Aikawa, Kurume, Fukuoka 839-0861, Japan.

PMID: 11975594 DOI: 10.1021/ol025519+

Abstract

[structure: see text]. 1: R = beta-D-glucopyranoside. 2: R = alpha-D-glucopyranoside. 3: R = alpha-D-galactopyranoside. 4: R = alpha-D-mannopyranoside. As an attempt to rationally design aqueous organogelators, a bolaamphiphilic azobenzene derivative (1) bearing two sugar groups was synthesized. Compound 1 formed a gel in water even at concentrations as low as 0.05 wt % (0.65 mM). Spectroscopic studies and electron-micrographic observations have clarified the gel structure and the origin of the gelation ability for water.

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