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Vibrational circular dichroism spectroscopy for probing the expression of chirality in mechanically planar chiral rotaxanes
Chemical Science ( IF 8.4 ) Pub Date : 2020-07-23 , DOI: 10.1039/d0sc02485f
Mark A. J. Koenis 1, 2, 3, 4 , C. S. Chibueze 1, 2, 3, 4 , M. A. Jinks 5, 6, 7, 8 , Valentin P. Nicu 9, 10, 11, 12 , Lucas Visscher 4, 13, 14, 15, 16 , S. M. Goldup 5, 6, 7, 8 , Wybren J. Buma 1, 2, 3, 4, 17
Affiliation  

Mechanically interlocked molecules can exhibit molecular chirality that arises due to the mechanical bond rather than covalent stereogenic units. Developing applications of such systems is made challenging by the absence of techniques for assigning the absolute configuration of products and methods to probe how the mechanical stereogenic unit influences the spatial arrangements of the functional groups in solution. Here we demonstrate for the first time that Vibrational Circular Dichroism (VCD) can be used to not only discriminate between mechanical stereoisomers but also provide detailed information on their (co)conformations. The latter is particularly important as these molecules are now under investigation in catalysis and sensing, both of which rely on the solution phase shape of the interlocked structure. Detailed analysis of the VCD spectra shows that, although many of the signals arise from coupled oscillators isolated in the covalent sub-components, intercomponent coupling between the macrocycle and axle gives rise to several VCD bands.

中文翻译:

振动圆二色光谱用于探测机械平面手性轮烷中的手性表达

机械互锁的分子可表现出由于机械键而不是共价立体形成单元而产生的分子手性。由于缺乏分配产品绝对构型的技术和方法来探究机械立体生成单元如何影响溶液中官能团的空间排列,因此开发此类系统的应用面临挑战。在这里,我们首次证明了振动圆二色性(VCD)不仅可以用来区分机械立体异构体,而且可以提供有关其(共)构象的详细信息。后者尤为重要,因为这些分子目前正在催化和传感领域进行研究,两者都依赖于互锁结构的溶液相形状。
更新日期:2020-08-20
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