Tetraphenylethene–2-Pyrone Conjugate: Aggregation-Induced Emission Study and Explosives Sensor

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• 作者：Vaithiyanathan Mahendran ; Kamaraj Pasumpon ; Solaimalai Thimmarayaperumal ; Pakkirisamy Thilagar ; Sivakumar Shanmugam
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：81
• 期：9
• 页码：3597-3602
• 全文大小：378K
• 年卷期：0
• ISSN：1520-6904

文摘

Design and synthesis of a novel tetraphenylethene–2-pyrone (TPEP) conjugate exhibiting donor–acceptor characteristics is reported. The localized frontier molecular orbitals (DFT studies) and the solvent polarity dependent photoluminescence characteristics directly corroborate the presence of intramolecular charge transfer character in TPEP. TPEP is poorly emissive in the solution state. In contrast, upon aggregation (THF/water mixtures), TPEP exhibits aggregation-induced emission enhancement. Upon aggregation, dyad TPEP forms a fluorescent nanoaggregate which was confirmed by transmission electron microscopy imaging studies. The luminescence nanoaggregates were elegantly exploited for selective detection of nitro aromatic compounds (NACs). It was found that nanoaggregates of TPEP were selectively sensing the picric acid over the other NACs. Efficiency of the quenching process was further evaluated by the Stern–Volmer equation. TPEP-based low-cost fluorescent test strips were developed for the selective detection of picric acid.