Department of Chemistry, Georgetown University, Washington, D.C., USA.
Chirality. 2020 Apr;32(4):457-463. doi: 10.1002/chir.23185. Epub 2020 Feb 6.
Practical chiroptical sensing with a small group of commercially available aromatic aldehydes is demonstrated. Schiff base formation between the electron-deficient 2,4-dinitrobenzaldehyde probe and either primary amines, diamines, or amino alcohols proceeds smoothly in chloroform at room temperature and is completed in the presence of molecular sieves within 2.5 hours. The substrate binding coincides with a distinct circular dichroism signal induction at approximately 330 nm, which can be correlated to the absolute configuration and enantiomeric composition of the analyte. The usefulness of this sensing method is highlighted with the successful sensing of 18 aliphatic and aromatic amines and amino alcohols and five examples showing quantitative %ee determination with good accuracy.
本文展示了一种实用的手性光学传感方法，仅使用少量市售芳香醛即可实现。在室温下，缺电子的 2,4-二硝基苯甲醛探针与伯胺、二胺或氨基醇之间的席夫碱形成反应在氯仿中顺利进行，在分子筛存在下 2.5 小时内完成。在底物结合的同时，在大约 330nm 处会出现明显的圆二色性信号诱导，可以将其与分析物的绝对构型和对映体组成相关联。该传感方法的实用性已通过成功传感 18 种脂肪族和芳香族胺以及氨基醇以及 5 个具有良好准确性的定量对映体过量（ee）测定实例得到了证明。
