Study on the second-order non-linear optical properties of 10-hydrocarbylacridones

Twenty 10-hydrocarbylacridones and 2-methylacridone, 1-hydroxyacridone were synthesized from acridone and characterized by mp, IR, UV, 1H NMR and MS. Using Nd:YAG as a laser source, the second-order harmonic generation (SHG) values of the acridone derivatives were measured in powder state as compared with urea powder. The results showed that the SHG values of some of 10-hydrocarbylacridones were higher than that of urea, while others were lower. Although the hydrocarbyl substituents (R) attached to nitrogen atom of acridone were different in size and electronegativity, they had a little effect on the SHG values of 10-hydrocarbylacridones. Substituents, such as methyl or hydroxy group connected to the phenyl ring, caused a little effect on the SHG values, too, compared with acridone. The ability of R to push electron toward the nitrogen atom or to pull electron from the nitrogen atom play an important role on the maximum wavelengthes of UV-visible absorption of acridone derivatives.