Structural, Hirshfeld surface and nonlinear optical properties of 4-fluorobenzylidene-4-methoxyaniline (FBMOA) and 4-fluorobenzylidene-4-methylaniline (FBMA)

Abstract

In the present work the syntheses, molecular structures and properties of two novel Schiff base N-benzylide-neanilines, 4-fluorobenzylidene-4-methoxyaniline (FBMOA) and 4-fluorobenzylidene-4-methylaniline (FBMA), are described. Their structures were confirmed by spectral and crystallographic analyses. FBMA crystallizes with two independent molecules in the asymmetric unit. The interatomic interactions in the crystals of FBMOA and FBMA, that contain different substituents, were investigated through Hirshfeld surface analysis. Thermally, FBMOA and FBMA were found to be stable; FBMOA undergoes bulk decomposition at ~ 180 ◦C and FBMA at~230 ◦C. UV–vis-NIR spectroscopy and open-aperture Z-scan studies were employed to characterize the linear and nonlinear optical behavior of the two compounds. Their structures and properties are compared to those of similar organo halide-substituted Schiff base compounds.