炔基三苯胺的合成及其光谱性质

Synthesis and Spectral Properties of Alkynyl Substituted Triphenylamines

炔基三苯胺为富电子荧光物质,当缺电子硝基化合物与其发生作用时,将引起炔基三苯胺共轭程度和电荷分布的变化,导致荧光随之发生变化。用炔烃和卤化三苯胺为原料,采用sonogashira金属偶联反应,设计与合成了系列炔基取代三苯胺化合物。应用荧光分析技术研究了分子结构、溶剂极性、硝基爆炸物的加入对炔基三苯胺溶液荧光性质的影响。结果表明,随着TNT浓度的增加,炔基三苯胺的荧光强度逐渐减弱,在浓度为1×10-5mol·L-1的炔基三苯胺溶液中,加入浓度为2.5×10-4mol·L-1的TNT,发生明显的荧光猝灭效应;当TNT的浓度增至1×10-2mol·L-1时,炔基三苯胺荧光几乎完全消失。此外,不同的硝基化合物对炔基三苯胺的荧光猝灭能力不同,与硝基化合物分子的骨架结构以及取代情况有关。因此炔基三苯胺有望成为硝基爆炸物检测的敏感材料。

When electron-deficient nitro-compounds interact with electron-rich fluorescent compounds of alkynyl substituted triphenylamines, it will cause the changes of the conjugate degree and the charge distribution of the fluorescent compounds, resulting in the change of fluorescence. Alkynyl substituted triphenylamines were designed and synthesized via sonogashira coupling reaction using alkynes and halogenated triphenylamines as raw materials. The effects of molecular structure, solvent polarity, and addition of nitro-explosives on the fluorescent properties of alkynyl substituted triphenylamine solution were studied by fluorescence analysis technique. Results show that with the increase of TNT concentration, the fluorescence intensity of the alkynyl substituted triphenyl- amines weakens gradually. When adding 2.5 x10-4 tool · L-1 of TNT into 1 xl0-5 mol · L-1 of alkynyl substituted triphenylamine solution, the obvious fluorescence quenching effect occurs and when the concentration of TNT rises up to 1 xl0-2 mol · L-1 , the fluorescence disappears completely. The quenching abilities of the alkynyl substituted triphenylamines to different nitro-explosive are different, so the alkynyl substituted triphenylamines are expected to become the sensitive materials for the detection of nitro-explosives.