Synthesis and Chiral Resolution of Twisted Carbon Nanobelts,Journal of the American Chemical Society

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Synthesis and Chiral Resolution of Twisted Carbon Nanobelts
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-09-22 , DOI: 10.1021/jacs.1c08468
Wei Fan ₁ , Taisuke Matsuno ₂ , Yi Han ₁ , Xuhui Wang ₁ , Qifeng Zhou _{1,

3} , Hiroyuki Isobe ₂ , Jishan Wu _{1,

3}

Affiliation

Twisted carbon nanobelts could display persistent chirality, which is desirable for material applications, but their synthesis is very challenging. Herein, we report the successful synthesis and chiral resolution of such a kind of molecules (1-H and 1) with a figure-eight configuration. 1-H was synthesized first by macrocyclization through Suzuki coupling reaction followed by benzannulation via Bi(OTf)₃-mediated cyclization reaction of vinyl ether. Oxidative dehydrogenation of 1-H gave the fully π-conjugated 1. Their twisted structures were confirmed by X-ray crystallographic analysis and calculations, and they can be resolved by chiral high-performance liquid chromatography. The isolated enantiomers showed persistent chiroptical properties according to the circular dichroism measurements, with moderate |g_abs| values (0.0016 for 1-H and 0.005–0.007 for 1). Their photophysical properties were also briefly studied.

中文翻译：

扭曲碳纳米带的合成和手性分离

扭曲的碳纳米带可以显示出持久的手性，这对于材料应用来说是理想的，但它们的合成非常具有挑战性。在此，我们报告了这种具有八字形构型的分子（1-H和1）的成功合成和手性拆分。首先通过Suzuki偶联反应通过大环化合成1-H，然后通过Bi(OTf) ₃介导的乙烯基醚环化反应进行苯环化。1-H 的氧化脱氢得到完全 π 共轭的1. 它们的扭曲结构通过 X 射线晶体学分析和计算得到证实，并且可以通过手性高效液相色谱分离。根据圆二色性测量，分离的对映异构体显示出持久的手性特性，中等 | g_绝对值| 值（0.0016为1-H和0.005-0.007为1）。还简要研究了它们的光物理性质。

更新日期：2021-10-06

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