4-烯丙氧基萘酰亚胺的合成与光学性质研究

Synthesis and Spectral Properties of 4-Allyloxy Naphthalimide

以4-溴-1,8-萘二甲酸酐为原料,与正丁胺反应生成4-溴萘酰亚胺,再与甲醇钠在硫酸铜的作用下反应,生成4-甲氧基萘酰亚胺,经HI作用,脱去保护得到4-羟基萘酰亚胺,最后与3-溴丙烯反应合成了目标化合物。结构经1HNMR、13CNMR、MS等加以表征,并对其吸收与荧光性质进行测定。结果表明,目标化合物收率为78%,紫外吸收波长为370 nm,荧光发射峰波长为450 nm。对HepG2细胞进行染色,激发后细胞呈现出强烈的蓝色荧光,成功实现细胞内荧光成像,具有良好的生物应用前景。

4-Bromo-naphthalimide was obtained by condensation of 4-bromo-1,8-naphthalene dimethyl anhydride and n-butylamine,and then reacted with sodium methoxide in the presence of copper sulfate to generate 4-methoxyl naphthalimide.4-Hydroxyl naphthalimide was obtained by the removal of protective group by hydroiodate.Finally,the target compound was synthesized by reaction of 4-hydroxyl naphthalimide and with 3-bromo-propylene.The structures were confirmed by 1HNMR,13CNMR and MS,the absorption and fluorescence properties were determined.The yield of the target compound was 78%,the absorption wavelength was 370 nm,and the fluorescence emission peak wavelength was 450 nm.HepG2 cells were stained and stimulated to show a strong blue fluorescence.The compound successfully realized the fluorescence imaging in cells,which has a good biological application prospect.