A novel naphthalimide derivative, N-(morpholinoethyl)-4-(4-ethynyl-phenol)-1, 8-naphthalimide (A) was synthesized by Sonogashira couple reaction by using 4-bromo-1, 8-naphthalicanhydride as the raw material. Its molecular structure was characterized by 1H NMR, 13C NMR and HR-MS (ESI). By analyzing the fluorescence emission spectra of compound A in six different polar organic solvents and methanol/tetrahydrofuran mixed solvents, along with the two-photon induced fluorescence spectra of A in tetrahydrofuran, the results showed that it has a significant response to the polarity with a solvatochromic effect. With the increase in solvent's polarity, the fluorescence emission peak of A is red-shifted and the fluorescence intensity is decreased. The two-photon absorption action cross section of A at 820 nm is 90 GM. In addition, A could be successfully localized to lysosomes, and the co-localization coefficient with lysosome commercial dye Lyso Tracker Red is as high as 0.902 6. Therefore, compound A as a novel two-photon absorption material could be used as a two-photon lysosomal tracking agent for cell imaging.%以4-溴-1, 8-萘二甲酸酐为起始原料通过Sonogashira偶联反应合成了一种新型萘酰亚胺衍生物 (N-吗啉乙基)-4-(4-羟基苯乙炔基)-1, 8-萘酰亚胺 (A), 其结构通过1H NMR、13C NMR、HR-MS (ESI) 表征, 并对化合物A在6种不同极性有机溶剂和甲醇/四氢呋喃混合溶剂中的荧光发射光谱, 以及A在四氢呋喃中的双光子诱导荧光光谱进行了分析.结果表明:A具有溶质变色效应, 随溶剂极性的增大, A的荧光发射峰发生红移, 且荧光强度下降.并且A在波长820 nm处的有效双光子吸收截面为90 GM.此外, A可成功定位于溶酶体, 与溶酶体商品化染料Lyso Tracker Red的共定位系数高达0.902 6.因此, 化合物A作为一个新型的双光子吸收材料, 可作为双光子溶酶体示踪剂用于细胞成像.
展开▼
