A series of L-glutamate-based dendrons containing aromatic cores ranging from phenyl to naphthyl to anthryl were synthesized, and their self-assembly in organic solvents as well as in water was investigated. It was found that all of these dendrons formed organogels with hexane and simultaneously formed the hydrogels with water, thus exhibiting ambidextrous properties. Nanofiber structures are essentially formed in organogels and hydrogels, and some nanostrips are formed in sonic of the hydrogels. During gel formation, both hydrogen bonds between the amide groups and the pi-pi stacking between the aromatic rings played a predominant role in forming the 1D nanostructures. Both the hydrogels and the organogels containing naphthyl and anthryl groups showed fluorescence emission. In comparison with the corresponding compounds in solution, the naphthyl-containing dendrons showed a strong enhancement of fluorescence in the gel. In the case of anthryl-containing dendrons, fluorescence enhancement was observed for the derivative with anthryl substituted at the 9 position, whereas a decrease was observed for the eels of the 2-substituted derivative. Although the chirality of L-glutamate could not be transferred to the aromatic chromophores in solution, it was transferred to the chromophores in gels as a result of the self-assembly and strong pi-pi interaction of the gelators. On the basis of the properties of the organogels and hydrogels, a thermally driven chiroptical switch was proposed. That is, the chirality disappeared when the gel was heated to solution, whereas it returned when cooled to a gel. The process can be repeated many times.