Remote Control of Dynamic Twistacene Chirality,Journal of the American Chemical Society

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Remote Control of Dynamic Twistacene Chirality
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-10-04 , DOI: 10.1021/jacs.2c08323
Si Tong Bao ₁ , Haoyu Jiang ₁ , Cedric Schaack ₁ , Shayan Louie ₁ , Michael L Steigerwald ₁ , Colin Nuckolls ₁ , Zexin Jin ₁

Affiliation

We report a reliable way to manipulate the dynamic, axial chirality in perylene diimide (PDI)-based twistacenes. Specifically, we reveal how chiral substituents on the imide position induce the helicity in a series of PDI-based twistacenes. We demonstrate that this remote chirality is able to control the helicity of flexible [4]helicene subunits by UV–vis, CD spectroscopy, X-ray crystallography, and TDDFT calculations. Furthermore, we have discovered that both the chiral substituent and the solvent each has a strong impact on the sign and intensity of the CD signals, highlighting the control of the dynamic helicity in this flexible system. DFT calculations suggest that the steric interaction of the chiral substituents is the important factor in how well a particular group is at inducing a preferred helicity.

中文翻译：

动态双苯手性的远程控制

我们报告了一种可靠的方法来操纵苝二酰亚胺 (PDI) 基双苯的动态轴向手性。具体而言，我们揭示了酰亚胺位置上的手性取代基如何在一系列基于 PDI 的双苯中诱导螺旋性。我们证明这种远程手性能够通过 UV-vis、CD 光谱、X 射线晶体学和 TDDFT 计算来控制柔性 [4] 螺旋烯亚基的螺旋性。此外，我们发现手性取代基和溶剂都对 CD 信号的符号和强度有很大影响，突出了这个灵活系统中动态螺旋性的控制。DFT 计算表明，手性取代基的空间相互作用是影响特定基团诱导优选螺旋性的重要因素。

更新日期：2022-10-04

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