Two low molecular weight gelators containing 4-ethynyl-1,8-naphthalimide groups with large conjugated structure via different length of alkyl chains were synthesized and fully characterized. The gelation properties, structural character, and fluorescence of the gels were investigated via methods of scanning electron microscopy, X-ray diffraction, and spectral studies. The gelators have high fluorescence quantum yields in both solution and solid state. Interestingly, the wavelength of the fluorescent emission in the reversible sol-gel transition process of the gels has a large red-shift of 80 nm in DMF, which is extremely sparse for 1,8-naphthalimide derivatives in the literature. The intermolecular π-π stacking between naphthalimide is suggested to be the main driving force for the gel formation and fluorescent variation by means of temperature-dependent (1)H NMR study and theoretical calculation.

Two new peptide-based isomers containing cholesterol and naphthalic groups have been designed and synthesized. We found that the position of L-alanine in the linker could tune the gelation properties and morphologies. The molecule with the L-alanine residue positioned in the middle of the linker (1b) shows better gelation behavior than that with L-alanine directly linked to the naphthalimido moiety (1a). As a result, a highly thermostable organogel of 1b with a unique core-shell structure was obtained at high temperature and pressure in acetonitrile. Moreover, the gels of 1a and 1b could undergo an instantaneous gel-to-gel transition triggered by sonication. Ultrasound could break the core-shell microsphere of 1b and the micelle structure of 1a into entangled fibers. By studying the mechanism of the sonication-triggered gel-to-gel transition process of these compounds, it can be concluded that ultrasound has a variety of effects on the morphology, such as cutting, knitting, unfolding, homogenizing, and even cross-linking. Typically, ultrasound can cleave and homogenize pi-stacking and hydrophobic interactions among the gel molecules and then reshape the morphologies to form a new gel. This mechanism of morphology transformation triggered by sonication might be attractive in the field of material storage and controlled release.

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