油溶性1,8-萘酰亚胺类荧光染料的合成研究

Studies on the Synthesis of Fluorescent Dyes of Soluble 1,8-Naphthalimides

摘要:

以4-溴-1,8-萘酐为原料，经过亚胺化和取代反应合成4-烷氧基-N-十二烷基-1,8-萘酰亚胺。通过单因素实验，确定了亚胺化反应的最佳条件，即n（4-溴-1,8-萘酐）: n（十二胺）=1:1.1，反应温度50 ℃，反应时间4 h，在此条件下，中间产物4-溴-N-十二烷基-1,8-萘酰亚胺的产率达到79.4%。采用IR、1H NMR对目标产物4-烷氧基-N-十二烷基-1,8-萘酰亚胺的结构进行表征，紫外吸收图谱和荧光光谱研究表明，目标产物在无水乙醇中的最大紫外吸收波长分别为357 nm和342 nm，最大发射波长分别为485 nm和490 nm。目标产物在DMF中的荧光量子产率达到0.6以上。

Abstract:

4-alkoxy-N-lauryl-1,8-naphthalimides were synthesized using 4-bromo-1,8-naphthalic anhydride and laurylamine as starting materials through the imidization and substitution reaction. The single factor experiments showed that optimum imidization reaction conditions were n(4-bromo-1,8-naphthalic anhydride) : n(laurylamine) =1:1.1, reaction temperature 50℃, reaction time 4 h. Under this conditions, the yield of intermediate product 4-bromo-N-lauryl-1,8-naphthalimide was 79.4%. Structures of the final products 4-alkoxy-N-lauryl-1,8-naphthalimides were characterized by IR and 1HNMR. The test results of UV absorption and fluorescent spectrum showed that the target product of the maximum absorption in absolute alcohol was 357nm and 342nm, and the maximum emission was 485nm and 490 nm, respectively. The fluorescent quantum yields of the dyes in DMF were over 0.6.