Oil-soluble 1,8 - Naphthalimide Fluorescent Dye Synthesis And Application Of Research

This research focuses on the synthesis and applications of oil-soluble fluorescent dyes. In this dissertation, the development of fluorescence compounds and 1,8-naphthalimide derivatives fluorescent dyes are reviewed. Eight 1,8-naphthalimide fluorescent dyes are synthesized, and we also study the technological conditions and fluorescence properties detailed.The intermediate products 4-bromo-N-lauryl-1,8-naphthalimide and 4-bromo-N-octadecyl-1,8-naphthalimide are synthesized using 4-bromo-1,8-naphthalic anhydride as starting materials through the imidization reaction. The single factor experiments show that optimum imidization reaction conditions are reaction temperature 50℃and 60℃, n(4-bromo-1,8-naphthalic anhydride): n(laurylamine)= 1:1.1 and n(4-bromo-1,8-naphthalic anhydride):n(octadecylamine)=1:1.15, reaction time 4 h and rest for 24h all, respectively. Under this conditions, the yield of intermediate products are79.4% and 65.8%, respectively. Detected infrared spectra of the intermediate products, and they meet the requirement of the design.The study synthesized eight oil-soluble fluorescent dyes through the substitution reaction which used intermediate products 4-bromo-N-lauryl-1,8-naphthalimide and 4-bromo-N-octadecyl-1,8-naphthalimide as raw materials in alkaline conditions and the existence of surfactant. Structures of the final products are characterized by IR,1HNMR and UV-Vis absorption maps, and three good properties of fluorescent dyes are selected. The test results of UV absorption and fluorescent spectrum show that the target products of 4-butoxy-N-lauryl-1,8-naphthalimide and 4-butoxyethoxy acetate-N-lauryl-1,8-naphthalimide of the maximum absorption in absolute alcohol is 342 nm and 357 nm, and the maximum emission is 490 nm and 485 nm, respectively. The fluorescent quantum yields of the dyes in DMF are over 0.6. The product of 4-butoxyethoxy acetate-N-octadecyl-1,8-naphthalimide has large fluorescence intensity, and fluorescent spectrum shows that has the obvious emission peaks between 440-600 nm, the maximum emission is 495 nm.In this research, a lot of application experiments in fluorescent leak detection and fluorescent label protein using synthetical fluorescent dyes. The solubility of 4-alkoxy-N-lauryl-1,8-naphthalimides in lubricants be tested, as valuable data for further actual application experiments. A novel method for determination of protein using 4-butoxyethoxy acetate-N-lauryl-1,8-naphthalimide as fluorescence probe is constructed and successfully apply to the determiation of the total protein in human serum albumin samples, and provide theory basis.