Glucose-based fluorescent low-molecular mass compounds: Creation of simple and versatile supramolecular gelators

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.