Precise Electron-Withdrawing Strength Regulation of π-Conjugate Bridge-Boosted Specific Detection toward
Zhenzhen Cai1,2, Zhiheng Huo2, Gaosheng Li2
1Xinjiang Key Laboratory of Trace Chemical Substances Sensing, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830000, China.
Abstract:
The specific fluorescent detection of α-methyltryptamine (AMT) presents a great challenge because similar amine groups and benzene rings exist in a variety of amines. Here, we show the precise modulation of the electron-withdrawing strength of the π-conjugate bridge in aldehyde-containing Schiff base-based fluorescent probes for ultratrace AMT discrimination. It is found that different electron-withdrawing groups -C6H4, -C6H2N2, and -C6H2Br2 as the π-conjugate bridge of the 2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF)-based probes can classify and identify organic amines with different amine nucleophilicities. Notably, the probe with -C6H2Br2 as the π-conjugate bridge, denoted as BrFS-TCF, which has the highest electrophilicity of the recognition site, shows a superior nM-level limit of detection (LOD) and an instant response time (<0.1 s) toward AMT. Especially, it shows an excellent selectivity facing the secondary amines, tertiary amines, aromatic amines, and even primary amines. The present strategy would provide a new pathway for chemical substances with similar structures and properties and especially for fighting against illegal drugs.
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