新型吖啶-9-磺酰胺衍生物的合成及光谱学性质  

Synthesis and Spectroscopic Property of Acridinium-9-sulfonamides

作　　者：穆小静[1] 肖尚友[1] 王建超[1] 吴彦蕾[1] 夏之宁[1] 

机构地区：[1]重庆大学化学化工学院,重庆400030

出　　处：《分析化学》2009年第7期970-974,共5页Chinese Journal of Analytical Chemistry

基　　金：科技部国际合作项目(No.2006DFA43520);国家自然科学基金(Nos.20805060;20775096);重庆市自然科学基金(Nos.2006BB5011;2006BB7182)资助项目

摘　　要：在吖啶磺酰胺分子中引入杂环安替比林吸电性基团,合成了N-对甲基苯磺酰基-N-(4-安替比林)-10-甲基吖啶-9-磺酰胺三氟甲基磺酸鎓盐。最终产物与未甲基化的前体分别与模型化合物N-对甲基苯磺酰基-N-苯基-10-甲基吖啶-9-酰胺三氟甲基磺酸鎓盐及其前体的紫外-可见吸收光谱(UV)、荧光光谱(FL)进行比较。结果表明,引入杂环安替比林使吖啶磺酰胺的UV和FL谱发生了变化,尤其是FL谱的最大激发与发射峰的位置比相应的模型化合物大幅蓝移。最终产物及其前体的最大λex分别为268和274nm;λem分别为321和327nm。而模型化合物及前体最大λex分别为365和359nm;λem分别为504和440nm。H2O2引发的目标产物的化学发光(CL)在1.1s完成;化学发光量子产率与模型化合物相当,是Luminol的化学发光效率的5.6倍。By introducing an electro-withdrawing antipyrine group, N- （p-toluenesulfonyl） -N- （4-antipyrine） - 10-methylacridinium-9-carboxamide triflate was prepared. The UV, FL and CL properties of the target compound and of its precursor were investigated by comparing with those of the model compound N-（ p-toluenesul- fonyl）-N-phenyl-10-methylacridinium-9-carboxamide triflate and the corresponding precursor respectively. The results show that acridine sulfonamide with a heterocyclic antipyrine group exhibits blue shift of both UV absorption and of maximum excitation wavelength （λem） and emission wavelength （λem） in FL spectra, comparing with the corresponding model compound. The λem of the final target and its precursor are 268 and 274 nm, respectively; and the λem are 321 and 327 nm, respectively, while Aox of the model compound and its unmethylated precursor are 365 and 359 nm, respectively; and the λem are 504 and 440 nm, respectively. Moreover, the chemiluminescence of the final target compound triggered by H2O2 could finish within 1. 1 s; and the quantum yield is similar to that of the model compound, being 5.6 times high as that of luminol.

关 键 词：吖啶磺酰胺 杂环取代 紫外光谱 荧光光谱 化学发光 

分 类 号：O626.32[理学—有机化学]