Five novel glucose-based naphthalene derivatives with linkers containing hydrazine, ethylenediamine, 1,3-propanediamine, 1,4-butanediamine, and 1,6-hexanediamine, respectively (1, 2, 3, 4, and 5) were designed and prepared. The gelation test revealed the following points: (1) within the 30 solvents tested, 1 gels water only; (2) in contrast, 2 gels not only water, but also 11 of the organic solvents tested, a typical "ambidextrous gelator"; (3) 3, 4, and 5, however, gel organic solvents only, and the numbers of solvents gelled are 11, 11 and 13, respectively. Clearly, these compounds are effective low-molecular mass gelators, and show transitions from a low-molecular mass hydrogelator to an ambidextrous gelator and then to low-molecular mass organogelators with a slight increase in the length of the spacers. Interestingly, 5 is a super gelator to acetonitrile, of which the minimum gelation concentration is only 0.07%, w/v. The morphology, microstructure and molecular aggregation of the system strongly depend on the transition, as revealed by SEM, contact angle, energy dispersive X-ray spectroscopy, and XRD measurements. More interestingly, an aggregation-induced enhanced emission was observed along with gelation. Furthermore, the system appeared as a supramolecular chiroptical switch in the sol-gel process that is the chirality disappeared when the gel was heated to solution, whereas it reappeared when cooled to a gel.