Vaniline (1) is nitrated by using known literature method to 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (2). The haloanilines (3a-g) used for the synthesis of Schiff bases was synthesized by known literature methods and by referring Vogel’s Practical Organic Chemistry, 5th Edition. The nitrovaniline is reactive towards amine and forming 4-{(E)-[(4-aryl)imine]methyl}-2-methoxy-6-nitrophenol (4a-g). The final compounds 4-{(E)-[(4-aryl)imine]methyl}- 2-methoxy-6-nitrophenol (4a-g) and are further subjected to fluorescence study.