Ultrasound induced formation of organogel from a glutamic dendron

Abstract

New l-glutamic acid based dendritic compounds: N-(2-naphthacarbonyl)- l-glutamic acid diethyl ester (NGE) and N-(2-naphthacarbonyl)-1,5-bis( l-glutamic acid diethyl ester)- l-glutamic diamide (NBGE) were designed. Although NGE could not form any gels in common solvents, NBGE could form stable gels in hexane, toluene, and water under ultrasound. Three dimensional network structures composed of fibers with various diameters were observed in the gel by SEM and TEM. FTIR spectral measurement revealed that ultrasound during cooling of the solution could destroy some of the hydrogen bond interactions and caused the gel formation. In solution, no CD signal was detected because the naphthyl chromophore is far from the chiral center. In the gel, however, CD signals assigned to the naphthyl group were observed, which indicated that the chirality of the chiral center could be transferred to the chromophore in the supramolecular organogel system.