Four coumarin derivatives(4a―4d) with different alkoxy chains were synthesized. It was found that compound 4d showed a better gelation ability than the other compounds, for example, it could self-assemble into organogels in various organic fluids via ultrasound treatment or heating-cooling process, whereas compound 4c could only gel in a few mixed solvents and compounds 4a, 4b could not form organogel. The results from fluorescent and FT-IR spectra indicate that π-π interaction had an effect on the formation of the organogels of compound 4d besides H-bonding and van der Waals interaction, which were the driving forces for the self-assembling of compound 4c in gel state. The gel of compound 4d in toluene could emit strong fluorescence under UV irradiation and the [2+2] cyc-lo-addition was suggested by 1H NMR and fluorescence spectroscopy. This light-sensitive organogel might find application in optical materials.
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