Formation and regulation of supramolecular chirality in organogel via addition of tartaric acid

A new 1,8-naphthalimide derivative was prepared in which the C-4 position was substituted by pyridin-4-ol. This derivative shows good gelation property that can gelate most of polar solvents. As an achiral molecule, helical fibre morphology was observed when the compound gelated acetone solvent. When 0.5 eq of D-tartaric acid or L-tartaric acid was added to the gel, the helical morphology was changed from left-handed to right-handed structure. This result was further proved by circular dichroism measurement. FT-IR experiment showed the formation of intermolecular H-bond between the gelator and tartaric acid. The photophysical properties of gelator had no difference before and after addition of tartaric acid; whereas the lamellar structure was varied by addition of tartaric acid.