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苯并[1,4]菲并[1,10]癸并[1,2-b:2',1'-f]吡咯(1.0.1.0.0.1.0.1.0.0)的合成、结构和拓扑手性。

1,4-Phenylene-Incorporated Decaphyrin(1.0.1.0.0.1.0.1.0.0): Synthesis, Structure, and Topological Chirality.

机构信息

Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China.

Materials Genome Institute, Shanghai University, Shanghai 200444, China.

出版信息

Org Lett. 2022 Apr 8;24(13):2509-2514. doi: 10.1021/acs.orglett.2c00636. Epub 2022 Mar 29.

Abstract

Expanded porphyrins represent emerging structures in realizing topological chirality; however, their inherent flexibility has hampered the effective chiral resolution. Herein, we rationally designed a decaphyrin , which could be separated into its enantiomers in the free-base form. The enantiomers showed noteworthy chiroptical properties, e.g., the intense circular dichroism response in the visible spectrum, and high absorption dissymmetry factors () of 0.036 at 618 nm. Theoretical analyses further explained the origin of the high value.

摘要

扩展卟啉代表了在实现拓扑手性方面的新兴结构;然而,它们固有的灵活性阻碍了有效的手性拆分。在此,我们合理设计了一种十吡咯啉,它可以在游离碱形式下分离为对映异构体。对映异构体表现出显著的手性光学性质,例如在可见光谱中具有强烈的圆二色性响应,以及在 618nm 处高达 0.036 的高吸收不对称因子()。理论分析进一步解释了高值的起源。

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