Enantioselective determination of chiral acids and amino acids by chiral receptors with aggregation-induced emissions,Organic Chemistry Frontiers

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Enantioselective determination of chiral acids and amino acids by chiral receptors with aggregation-induced emissions
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-08-05 , DOI: 10.1039/d2qo01073a
Mingyu Chen ₁ , Chunxuan Qi ₁ , Yu-Ting Yin ₁ , Panpan Lv ₁ , Song Xiang ₁ , Jingjing Tian ₁ , Jing Feng Zhao ₂ , Hai-Tao Feng ₁ , Ben Zhong Tang ₃

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Enantioselective recognition is a general process in the natural world, which is involved in asymmetric synthesis, chiral drug separation, food chemistry, and life sciences. Herein, a pair of chiral AIEgens composed of cyanostilbene and optically pure 1,2-diphenylethylenediamine groups were facilely synthesised; the products showed excellent enantioselectivity for a series of chiral acids and amino acids. ¹H NMR and 2D-NOESY spectra indicated that the chiral sensing ability could be attributed to the multiple hydrogen-bonding interactions and specific stereoselectivity between the chiral 1,2-diphenylethylenediamine group and the enantiomer of the chiral guest. These synergistic interactions resulted in the selective aggregation of the receptor with one of the enantiomers. Interestingly, the chiral AIEgens thus obtained also presented a high selectivity for arginine from 22 kinds of acidic compounds that could be seen with the naked eye. Our research exhibits great potential for high-throughput analysis of enantiomers by AIE-active chiral receptors.

中文翻译：

手性受体聚合诱导发射对手性酸和氨基酸的对映选择性测定

对映选择性识别是自然界的普遍过程，涉及不对称合成、手性药物分离、食品化学和生命科学等领域。在此，轻松合成了一对由氰基芪和光学纯的1,2-二苯基乙二胺基团组成的手性AIEgens；该产品对一系列手性酸和氨基酸表现出优异的对映选择性。¹H NMR和2D-NOESY光谱表明，手性传感能力可归因于手性1,2-二苯乙二胺基团与手性客体的对映异构体之间的多重氢键相互作用和特定的立体选择性。这些协同相互作用导致受体与对映异构体之一的选择性聚集。有趣的是，由此获得的手性AIEgens也对肉眼可见的22种酸性化合物中的精氨酸具有高选择性。我们的研究显示出通过 AIE 活性手性受体对对映体进行高通量分析的巨大潜力。

更新日期：2022-08-05

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