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Iptycene-based fluorescent sensors for nitroaromatics and TNT

机译：基于异丁烯的硝基芳香族和TNT荧光传感器

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摘要

Small-molecule fluorescent sensors (1-5) for the recognition of nitroaromatic compounds, such as 2,4-dinitrotoluene and the explosive TNT, were obtained by using a three-step dehydrohalogenation cycloaddition protocol. The interaction of the receptors and nitroaromatics was studied both in solution and in the solid state by using fluorescence spectroscopy and X-ray crystallography, respectively. It is shown that the iptycene receptors 1-5 provide a cavity suitable for binding nitroaromatic compounds in an edge-to-face mode, rather than simple ring-stacking interactions. The results obtained inspired us to develop an inexpensive, reliable and robust sensor for vapour detection of explosives. Polymer nanofibres are particularly suitable for the production of such TNT sensors as they accelerate the mass exchange between the polymer and the vapours of TNT. Quenching of the sensors took place within 1 min compared to 10 min for a glass-slide assay. Hence, the sensor performance can be improved by optimising the matrix material and morphology without resynthesising the sensor moieties. TNT is sensed! Fluorescent sensors based on the iptycene recognition motif were synthesised and studied with different nitroaromatic compounds. X-ray structures confirm the establishment of edge-to-face interactions. Fluorescence studies in solution and in polymer matrices allowed the development of polymer-nanofibre sensors for the detection of nitroaromatic compounds and TNT (see figure).
机译：通过使用三步脱氢卤化环加成方案，获得了用于识别硝基芳香族化合物（例如2,4-二硝基甲苯和爆炸性TNT）的小分子荧光传感器（1-5）。分别通过荧光光谱和X射线晶体学研究了溶液和固态中受体与硝基芳烃的相互作用。结果表明，并茂茂的受体1-5提供了一个适合以边对面方式结合硝基芳族化合物的腔，而不是简单的环堆积相互作用。获得的结果激励我们开发出一种廉价，可靠且坚固的传感器，用于爆炸物的蒸气检测。聚合物纳米纤维特别适合于生产此类TNT传感器，因为它们可加速聚合物与TNT蒸气之间的质量交换。传感器的淬火发生在1分钟内，而玻璃玻片测定则为10分钟。因此，可以通过优化基体材料和形态来提高传感器性能，而无需重新合成传感器部分。感觉到TNT！合成了基于茂茂识别基序的荧光传感器，并用不同的硝基芳香族化合物进行了研究。 X射线结构确认了边对面相互作用的建立。在溶液和聚合物基质中的荧光研究使聚合物纳米纤维传感器的开发成为可能，用于检测硝基芳族化合物和TNT（见图）。

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