油溶性1,8-萘酰亚胺类荧光染料的合成研究

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

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,在该条件下,中间产物4-溴-N-十二烷基-1,8-萘酰亚胺的产率达79.4%。采用IR、1HNMR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了表征,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0.6以上。

4-Alkoxy-N-lauryl-1,8-naphthalimides were synthesized using 4-bromo-1,8-naphthalic anhydride and laurylamine as initiating materials through imidization and substitution reaction.The single factor experiments show that the optimal imidization reaction conditions were n（4-bromo-1,8-naphthalic anhydride）∶ n（laurylamine）=1∶ 1.1,reaction temperature 50 ℃,reaction time 4 h.Under such conditions,the yield of intermediate product 4-bromo-N-lauryl-1,8-naphthalimide was 79.4%.The 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 show that the maximum absorption in absolute alcohol of the target products was 357 nm and 342 nm respectively,and the maximum emission was 485 nm and 490 nm respectively.The fluorescent quantum yields of the dyes in DMF were over 0.6.