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炸药与TPE大环空腔的CH3-π相互作用:高选择性检测TNT的关键原因。

CH3-π interaction of explosives with cavity of a TPE macrocycle: the key cause for highly selective detection of TNT.

作者信息

Feng Hai-Tao, Wang Jin-Hua, Zheng Yan-Song

机构信息

Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology , Wuhan 430074, China.

出版信息

ACS Appl Mater Interfaces. 2014 Nov 26;6(22):20067-74. doi: 10.1021/am505636f. Epub 2014 Oct 24.

DOI:10.1021/am505636f
PMID:25319016
Abstract

The identification of explosives is critical for analyzing the background of terrorism activities and the origin of pollution aroused by the explosives, but it is a challenge to discriminate the explosives with a very similar structure. Herein we report a series of TPE-based macrocycles with an AIE effect for the 0.2-4 ppb level detection of TNT among a number of nitro-aromatic compounds through fluorescence quenching in natural water sources, whereas the contact mode approach using portable paper sensors exhibited a high sensitivity for the detection of TNT at 1.0 × 10(-13) M level. The reliability of the quantitative analysis has been confirmed by HPLC. Our findings demonstrate that the TPE-based macrocycles have great potential as excellent sensors for TNT. Moreover, it was found for the first time that the macrocycles could selectively recognize nitroaromatics explosives bearing methyl group through a CH3-π interactions, and even exhibit a sole selectivity for TNT among the very difficultly differentiating nitroaromatics including trinitrophenol and trinitrobenzene.

摘要

爆炸物的识别对于分析恐怖主义活动背景以及爆炸物引起的污染来源至关重要,但区分结构非常相似的爆炸物是一项挑战。在此,我们报告了一系列具有聚集诱导发光(AIE)效应的基于四苯乙烯(TPE)的大环化合物,通过在天然水源中荧光猝灭实现对多种硝基芳烃化合物中0.2 - 4 ppb水平的三硝基甲苯(TNT)检测,而使用便携式纸质传感器的接触模式方法对1.0×10⁻¹³ M水平的TNT检测表现出高灵敏度。高效液相色谱(HPLC)已证实定量分析的可靠性。我们的研究结果表明,基于TPE的大环化合物作为TNT的优秀传感器具有巨大潜力。此外,首次发现大环化合物可通过CH₃ - π相互作用选择性识别带有甲基的硝基芳烃爆炸物,甚至在包括三硝基苯酚和三硝基苯在内极难区分的硝基芳烃中对TNT表现出唯一选择性。

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