【作者】 王建新；

【导师】 李宗石；

【作者基本信息】 大连理工大学 ， 应用化学， 2006， 硕士

【摘要】 荧光化合物因其信号灵敏,检测方便等原因使其在生物、医药以及探针等应用领域成为科学研究的热点。近几十年来,荧光探针在表面活性剂领域也得到了广泛的应用和发展。但是由于目前所用的荧光探针大多水溶性较差,所以在使用时受到了不同程度的限制。设想在不改变荧光基本性质的前提下,通过合适的连接方式,将荧光发色基团引入到表面活性剂分子当中,必将形成一类新的化合物——荧光类表面活性剂。此类化合物不仅会具有荧光物质的基本性质,而且还会具有表面活性剂的基本特征,对于荧光类非离子表面活性剂,甚至可以通过调节温度来控制荧光探针的水溶性,也可以制成具有荧光性质的脂质体,这将可能带来广阔的应用前景。 本文筛选出斯托克斯位移较大,荧光发射波长适中,荧光信号强烈的萘酰亚胺作为荧光母体,选用酰胺基团作为连接基,将其引入到典型的表面活性剂当中,从而设计并合成了两个荧光类非离子表面活性剂Ⅲ_a和Ⅲ_b以及系列荧光类阴离子表面活性剂。并通过质谱、红外、核磁等手段验证了目标化合物的结构。这两类表面活性剂的结构尚未见文献报导。 随着溶剂极性的增加,Ⅲ_a,Ⅲ_b荧光最大发射光谱均发生红移,荧光强度均有所降低,特别是Ⅲ_b,荧光强度变化十分显著,可以作为微极性环境的荧光探针。Ⅲ_a,Ⅲ_b的CMC分别是11.48×10^-6mol/L和4.07×10^-6mol/L,最低表面张力(γ_cmc)分别是31.29mN/m和31.73mN/m,浊点（cloud point）分别是40.1℃和44.2℃,由于Ⅲ_b分子中特殊的双疏水尾链结构,使其在水中容易形成封闭的囊泡结构（20-50nm）。 化合物1,2,3的钠盐在水溶液中的CMC从12.11×10^-5mol/L依次降低至3.29×10^-5mol/L和1.68×10^-5mol/L,而最低表面张力依次为40.23 mN/m,40.01mN/m和40.06mN/m。总体来说,随着溶剂极性的增加,化合物1,2,3和4的最大吸收波长和荧光最大发射波长都发生红移,荧光强度减弱。更多还原

【Abstract】 Fluorescent compounds, which have not only used widely in biological and medical fields but also applied as fluorescence probe in surfactant field, have become an important area of research because of their sensitive fluorescent signals and convenient detection recently. But their poor water-solubility usually circumscribed their application. It was hypothesized that by introducing a fluorescent group into a surfactant molecule by an appropriate method to get a series of surfactants, which would provide not only the surface properties (CMC, γ_cmc). but also the fluorescence properties as well. Especially the water solubility of fluorescent nonionic surfactants can be controlled by adjusting temperature and liposome with fluorescent properties can be prepaired with them. Thus, some potential applications might be brought in special fields.Two fluorescent non-ionic surface active agents III_a and III_b were designed and synthesized from naphthalimide and （Polyoxyethylene dodecyl ether）AEO₉ by amido link and a series of fluorescent anionic surfactants were also obtained from the naphthalimide. They were characterized by MS, IR and ¹H NMR and their surface and fluorescent properties were measured. Their structures have not been seen in the papers by far.The fluorescence emission maxima (λ_em) exhibited a bathochromic shift and decreased fluorescence emission as both the compounds of III_a and III_b were introduced into more polar solvents. Both III_a and III_b were environment-sensitive and could be used as fluorescent probes because their fluorescence spectra were highly dependent on the solvent. The values of CMC for III_a and III_b were 11.48×10^-6mol/L and 4.07×l0^-6 mol/L and surface tensions at CMC were 31.29 raN/m and 31.73 mN/m respectively and their cloud points were 40.1℃ and 44.2℃ respectively. Moreover, compound III_b formed closed vesicle in aqueous solution spontaneously because of its special bihydrophobic-chain structure and IIIb liposome would give small particles with spherical structures about 20-50 nm in diameter.The values of CMCs for compound 1, 2 and 3 were 12.11×10^-5mol/L, 3.29×10^-5 mol/L and 1.68×10^-5 mol/L and their surface tensions at CMC were 40.23 mN/m, 40.01 mN/m and 40.06 mN/m respectively. The fluorescence emission maxima (λ_em) exhibited a bathochromic shift and decreased fluorescence emission as both the compounds of compound 1, 2, 3 and 4 were introduced into more polar solvents.更多还原