Zhu Huangtianzhi, Li Qi, Gao Zongchun, Wang Hongliang, Shi Bingbing, Wu Yitao, Shangguan Liqing, Hong Xin, Wang Feng, Huang Feihe
State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. China.
CAS Key Laboratory of Soft Matter Chemistry, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China.
Angew Chem Int Ed Engl. 2020 Jun 26;59(27):10868-10872. doi: 10.1002/anie.202001680. Epub 2020 Apr 23.
The contradiction between the rising demands of optical chirality sensing and the failure in chiral detection of cryptochiral compounds encourages researchers to find new methods for chirality amplification. Inspired by planar chirality and the host-guest recognition of pillararenes, we establish a new concept for amplifying CD signals of cryptochiral molecules by pillararene host-guest complexation induced chirality amplification. The planar chirality of pillararenes is induced and stabilized in the presence of the chiral guest, which makes the cryptochiral molecule detectable by CD spectroscopy. Several chiral guests are selected in these experiments and the mechanism of chiral amplification is studied with a non-rotatable pillararene derivative and density functional theory calculations. We believe this work affords deeper understanding of chirality and provides a new perspective for chiral sensing.
光学手性传感需求不断增长与隐手性化合物手性检测失败之间的矛盾，促使研究人员寻找新的手性放大方法。受平面手性和柱芳烃主客体识别的启发，我们建立了一个新的概念，即通过柱芳烃主客体络合诱导的手性放大来增强隐手性分子的圆二色（CD）信号。在手性客体存在的情况下，柱芳烃的平面手性被诱导并稳定下来，这使得隐手性分子能够通过CD光谱检测到。在这些实验中选择了几种手性客体，并使用不可旋转的柱芳烃衍生物和密度泛函理论计算研究了手性放大的机制。我们相信这项工作能让人们对手性有更深入的理解，并为手性传感提供一个新的视角。
