新型苊并吡嗪类高灵敏度极性探针

A highly sensitive polar probe derived from acenaphthopyrazine

以苊醌为原料,经溴化、环构化和芳香亲核取代反应合成了一种新型的以苊并吡嗪为母体的极性荧光探针3-正丁胺基-苊并吡嗪-8,9二腈(A)。探针A的荧光强度随着溶剂极性的增加显著降低,从四氯化碳(Φf=0.364 2)到乙腈(Φf=0.000 6)荧光量子产率减弱超过600倍,从四氯化碳(533nm)到N,N-二甲基甲酰胺(651nm)最大发射波长红移了118nm。利用探针A对极性敏感来检测有机溶剂中的水含量,建立了一种新的四氢呋喃和1,4-二氧六环中水含量荧光分析方法,最低检测限分别为0.019%和0.0076%。

A new polar sensitive probe 3-（n-butyl amino）acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile（A） has been synthesized from acenaphthylene-1,2-dione via bromization,cyclization and SNArHreaction.The fluorescence intensity of probe A reduces significantly with the increase of polarity of solvents.The fluorescence quantum yield decreases more than 600-fold from tetrachloromethane（Φf=0.364 2） to acetonitrile（Φf=0.000 6）,and the maximum emission intensity red-shifts by 118 nm,i.e.,from 533 nm in tetrachloromethane to 651 nm in N,N-dimethylformamide.A new method of fluorescence analysis to determine water content in tetrahydrofuran and 1,4-dioxane has also been proposed,with detection limits of 0.019% and 0.007 6%,respectively.