Fluorescent products of lipid peroxidation: I. Structural requirement for fluorescence in conjugated schiff bases

Abstract

Abstract The structural requirement for fluorescence in Schiff bases was defined. Aldehydes and amines were reacted and the structures of the Schiff bases N‐hydroxyethyl‐1‐imino‐2′,4′‐hexadiene (I), N‐1‐benzal‐2‐hydroxyaminoethane (II), and N‐1‐benzal‐2,2′‐hydroxyaminoethane (III) were established by elemental analysis, IR spectral analysis and mass spectral analysis. The structures of N‐alanyl‐2‐hydroxy‐naphthylidine (IV) and N,N′‐dileucinyl‐1‐amino‐3‐iminopropene (V) had been established previously. III, IV and V were fluorescent compounds and I and II were not. The results of these analyses suggest that an electron donating group in conjugation with an imine is the structure required for fluorescence.