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荧蒽修饰的四苯基乙烯衍生物:分子合成、聚集增强荧光特性及其对苦味酸的高灵敏度检测
Fluoranthene-Modified Tetraphenylethene Derivatives:Synthesis,Aggregation-Enhanced Emission Characteristic and Their Highly Sensitive Detection of Picric Acid
【摘要】 由于聚集体和固态发光量子效率高等优点,因此聚集诱导发光(AIE)材料成为光电功能材料研究领域的热点,拓展AIE分子体系始终是这一领域中的关键和基础的科学问题.通过Suzuki-Miyaura偶联这一条件较为温和的反应,将AIE生色团四苯基乙烯(TPE)与荧蒽直接共轭键接,制备得到单荧蒽和双荧蒽修饰的TPE衍生物TPE-FA与TPE-DFA,它们具有聚集增强荧光(AEE)行为,聚集体发射峰值波长分别在477和494 nm,固体薄膜的绝对荧光量子产率高达74.1%和40.4%.它们可以高灵敏地检测苦味酸,荧光猝灭常数大,检出限低于1μg·g-1.这两种AEE分子可望用于其它多硝基取代的芳香类吸电子分子的检测.
【Abstract】 Aggregation-induced emission(AIE) active compounds and materials have become one of the hottest research topics worldwide,due to their unprecedented merits such as ultra-high fluorescence quantum efficiencies as aggregates or in solid state.Up to now,it is still extremely crucial and fundamental to expand the AIE-genic molecular systems for this research area.Here,we prepared two fluoranthene-modified tetraphenylethene(TPE) derivatives,TPE-FA and TPE-DFA,through the Suzuki-Miyaura coupling between boronate-bearing TPE and bromo-bearing fluoranthene under mild reaction condition.The conjugation between fluoranthene and TPE moieties assures that the as-prepared TPE-FA and TPE-DFA both possess aggregation-enhanced emission(AEE) characteristics.The emission maximum of TPE-FA and TPE-DFA as aggregates in THF/water mixtures is at 477 nm and 494 nm,and the absolute quantum yields of the two compounds in solid films are as high as 74.1% and 40.4%,respectively.They can be utilized as fluorescent probes for picric acid with high sensitivity.Their quenching coefficients can be as high as 4×104 L·mol-1,while their detection limits can be lower than 1 μg·g-1.These AEE-active molecules are promising to act as fluorescent probes in the detection of other nitro-substituted electron-deficient molecules.
【Key words】 tetraphenylethene; fluoranthene; aggregation-induced emission(AIE); aggregation-enhanced emission(AEE); picric acid;
- 【文献出处】 化学学报 ,Acta Chimica Sinica , 编辑部邮箱 ,2016年11期
- 【分类号】O625.12
- 【被引频次】5
- 【下载频次】305