Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China.
J Org Chem. 2011 Aug 5;76(15):6101-7. doi: 10.1021/jo2007576. Epub 2011 Jul 7.
Detecting volatile amines is a significant topic in quality control of food and medical diagnosis. Selectively sensing a given gaseous amine from other analogues, however, still remains a formidable challenge in solid-state fluorescence sensing because of the lack of specialized binding sites. Herein, we demonstrate a new supramolecular strategy for selectively sensing aniline based on the aggregation of perylene-cyclodextrin conjugate 1. Compared with our previous results based on perylene-bridged bis(permethyl-β-cyclodextrins), the present system achieves a pronounced improvement of both selectivity and reversibility. The sensory material was constructed from the π-stacking aggregate of 1 embedded in poly(vinylidene fluoride) membrane, which ensures benign solid-state fluorescence with potential amplification mechanism as well as convenient preparation and practical operation. Grafting cyclodextrin receptors endows the sensory material with desired selectivity as a result of diverse binding abilities. Especially, the thermodynamically reversible host-guest inclusion leads to the excellent sensing reversibility. The present research opens the way to build new n-type fluorescence sensory materials for detecting volatile amines instantly with compelling selectivity, sensitivity, and reversibility.
检测挥发性胺类物质是食品质量控制和医学诊断中的重要课题。然而，由于缺乏特定的结合位点，在固态荧光传感中，从其他类似物中选择性地检测特定的气态胺仍然是一个巨大的挑战。在此，我们展示了一种基于苝-环糊精 1 聚集的新型超分子策略，用于选择性地检测苯胺。与我们之前基于并苯桥联双（全甲基-β-环糊精）的结果相比，本体系在选择性和可逆性方面均有显著提高。传感材料由嵌入聚偏二氟乙烯膜中的 1 的π-堆积聚集体构建而成，这确保了具有潜在放大机制的良性固态荧光以及方便的制备和实际操作。由于具有不同的结合能力，接枝环糊精受体赋予了传感材料所需的选择性。特别是，热力学可逆的主客体包合作用导致了优异的传感可逆性。本研究为构建新型 n 型荧光传感材料以即时、高选择性、高灵敏度和高可逆性检测挥发性胺类物质开辟了道路。
