天津大学-新加坡国立大学福州联合学院吴继善团队报道了扭曲碳纳米带的合成及其手性拆分。相关研究成果发表在2021年9月22日出版的《美国化学会杂志上》。

扭曲的碳纳米带可以显示出持久的手性，对于材料应用来说是理想的，但是它们的合成非常具有挑战性。

该文中，研究人员报道了一种具有figure-eight构型的分子（1-H和1）的成功合成和手性拆分。首先通过Suzuki偶联反应进行大环化，然后通过Bi（OTf）₃介导的乙烯基醚环化反应进行苯环化，合成了1-H。1-H氧化脱氢得到完全π共轭的1。通过X射线晶体学分析和计算证实了它们的扭曲结构，并可通过手性高效液相色谱进行拆分。

根据圆二色谱测量，分离的对映体显示出持久的手性性质，具有中等的| gabs |值（1-H为0.0016，1-H为0.005–0.007）。并对其光物理性质进行了简要研究。

附：英文原文

Title: Synthesis and Chiral Resolution of Twisted Carbon Nanobelts

Author: Wei Fan, Taisuke Matsuno, Yi Han, Xuhui Wang, Qifeng Zhou, Hiroyuki Isobe, Jishan Wu

Issue&Volume: September 22, 2021

Abstract: 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 |gabs| values (0.0016 for 1-H and 0.005–0.007 for 1). Their photophysical properties were also briefly studied.

DOI: 10.1021/jacs.1c08468

Source: https://pubs.acs.org/doi/10.1021/jacs.1c08468