Synthesis of Catenanes from a BMP32C10-Based Cryptand Tuned by the Linkage Length of Paraquat Salts

Feng-Zhi Yan; Yuan-Guang Shao; Zibin Zhang; Yan-Feng Shen; Xue-Chun Huang; Pei-Ling Zhang; Shijun Li

doi:10.1055/s-0040-1707290

Synthesis, Table of Contents

Synthesis 2021; 53(02): 338-343
DOI: 10.1055/s-0040-1707290

special topic

Functional Organic Molecules

Synthesis of Catenanes from a BMP32C10-Based Cryptand Tuned by the Linkage Length of Paraquat Salts

Feng-Zhi Yan

,

Yuan-Guang Shao

,

Zibin Zhang

,

Yan-Feng Shen

,

Xue-Chun Huang

,

Pei-Ling Zhang

,

Shijun Li∗

College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China Email: l_shijun@hznu.edu.cn

› Author Affiliations

Abstract

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Abstract

A series of catenanes have been synthesized through olefin metathesis from a BMP32C10-based cryptand and paraquat guests attached with two terminal alkenes. Distribution of the catenane products can be significantly affected by the linkage length on the paraquat guests. In the presence of BMP32C10-based cryptand, the paraquat salt with a long linkage facilitates intramolecular olefin metathesis to release a [2]catenane as the sole catenation product, while the use of a paraquat salt with a shorter linkage leads to the simultaneous generation of [2]-, [3]-, and [4]-catenanes.

Key words

catenanes - crown compounds - cryptands - paraquat - olefin metathesis - mechanically interlocked molecules - host–guest systems - pseudorotaxanes

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References

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