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在辐射下合成噻吩基双螺旋体的内消旋体和外消旋体。

Synthesis for the mesomer and racemate of thiophene-based double helicene under irradiation.

机构信息

Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng, 475004, China.

出版信息

J Org Chem. 2013 Jun 21;78(12):6316-21. doi: 10.1021/jo400691s. Epub 2013 Jun 10.

DOI:10.1021/jo400691s
PMID:23713420
Abstract

In this work, the racemate and mesomer of the thiophene-based naphthalene-cored double helicenes (1) were obtained efficiently by one-pot photocyclization of 1,1,2,2-tetrakis(dithieno[2,3-b:3',2'-d]thiophen-2-yl)ethene in the presence of iodine in dry benzene. The structure of meso-1a was confirmed by single crystal X-ray analysis. The chiral resolution of the racemate was carried out by chiral HPLC, and the chiral properties, such as CD spectra, optical rotations, and half-life of enantiomers were characterized.

摘要

在这项工作中,通过在干燥苯中存在碘的情况下一锅光环化 1,1,2,2-四(二噻吩[2,3-b:3',2'-d]噻吩-2-基)乙烯,高效地获得了基于噻吩的萘核双螺旋体(1)的外消旋体和内消旋体。通过单晶 X 射线分析确定了内消旋体 1a 的结构。通过手性 HPLC 对外消旋体进行了手性拆分,并对其手性性质,如 CD 光谱、旋光率和对映体半衰期进行了表征。

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