Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering , Nagoya University , Chikusa-ku, Nagoya 464-8603 , Japan.
J Am Chem Soc. 2018 Mar 7;140(9):3270-3276. doi: 10.1021/jacs.7b10981. Epub 2018 Jan 24.
We report the first direct chirality sensing of a series of chiral hydrocarbons and isotopically chiral compounds (deuterated isotopomers), which are almost impossible to detect by conventional optical spectroscopic methods, by a stereoregular polyacetylene bearing 2,2'-biphenol-derived pendants. The polyacetylene showed a circular dichroism due to a preferred-handed helix formation in response to the hardly detectable hidden chirality of saturated tertiary or chiroptical quaternary hydrocarbons, and deuterated isotopomers. In sharp contrast to the previously reported sensory systems, the chirality detection by the polyacetylene relies on an excess one-handed helix formation induced by the chiral hydrocarbons and deuterated isotopomers via significant amplification of the chirality followed by its static memory, through which chiral information on the minute and hidden chirality can be stored as an excess of a single-handed helix memory for a long time.
我们报告了首例通过具有 2,2'-联苯酚衍生侧基的规整聚乙炔对一系列手性烃和同位素手性化合物（氘代同位素）的直接手性感应，这些化合物几乎无法通过传统的光学光谱方法检测。聚乙炔由于对难以检测的隐藏手性饱和叔碳或手性季碳烃和氘代同位素的优先手性螺旋形成而表现出圆二色性。与以前报道的传感系统形成鲜明对比的是，聚乙炔的手性检测依赖于手性烃和氘代同位素通过显著放大手性后通过其静态记忆诱导的过量单螺旋形成，通过这种方式，微小和隐藏手性的手性信息可以作为单螺旋记忆的过量长期存储。
