含萘酰亚胺光功能基元的吡唑啉酮席夫碱的合成及其光谱性质

Synthesis and Spectrum Properties of the Schiff-base Containing Naphthalimide and Pyrazolone Chromophores

以4-溴-1,8-萘酐为原料,经亚胺化、取代和还原反应合成了中间体N-对氨基苯基-4-哌啶-1,8-萘酰亚胺(4),4与1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮-5缩合得到一种含萘酰亚胺光功能基元的的新型吡唑啉酮席夫碱——1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮-5缩N-对氨基苯基-4-哌啶-1,8-萘酰亚胺(6)。4和6的结构经1H NMR和IR确证。研究了6在不同溶剂中的光谱性质,发现其吸收光谱和荧光光谱随溶剂的极性不同而表现出不同的光谱特性。进一步研究表明6在不同溶剂中可能以不同的互变异构体存在。

N- （p-aminophenyl） -4-piperidinyl-1,8-naphthalimide （4） was synthesized from 4-bromo-1,8-naphthalic anhydride by imidization, substitution and reduction. A Schiff-base containing naphthalimide and pyrazolone chromophores, 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone-N-（p-aminophenyl）-4-pipefidinyl-1,8-naphthalimide（6） was obtained by condensation between 4 and 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone. The structures of 4 and 6 were characterized by ^1H NMR and IR. The fluorescent spectroscopy and UV-Vis spectrum of 6 were investigated in different solvents. The fluorescence spectrum and UV-Vis spectrum of 6 varied with the polarity of solvents. On the basis of experimental data it is suggested that different tautomers of 6 exist in different solvents.