Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers

Xuancheng Fu; Boyu Zhu; Xiaoran Hu

doi:10.1021/jacs.3c03994

Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers

Xuancheng Fu, Boyu Zhu, Xiaoran Hu

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

This paper describes a mechanical approach to inducing the atropisomerization of a parallel diarylethene into its antiparallel diastereomers exhibiting distinct chemical reactivity. A congested parallel diarylethene mechanophore in the (R_a,S_a)-configuration with mirror symmetry is atropisomerized to its antiparallel diastereomers with C₂ symmetry under ultrasound-induced force field. The resulting stereochemistry-converted material gains symmetry-allowed reactivity toward conrotatory photocyclization.

Original language	English (US)
Pages (from-to)	15668-15673
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	145
Issue number	29
DOIs	https://doi.org/10.1021/jacs.3c03994
State	Published - Jul 26 2023

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "This paper describes a mechanical approach to inducing the atropisomerization of a parallel diarylethene into its antiparallel diastereomers exhibiting distinct chemical reactivity. A congested parallel diarylethene mechanophore in the (Ra,Sa)-configuration with mirror symmetry is atropisomerized to its antiparallel diastereomers with C2 symmetry under ultrasound-induced force field. The resulting stereochemistry-converted material gains symmetry-allowed reactivity toward conrotatory photocyclization.",

author = "Xuancheng Fu and Boyu Zhu and Xiaoran Hu",

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AU - Zhu, Boyu

AU - Hu, Xiaoran

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AB - This paper describes a mechanical approach to inducing the atropisomerization of a parallel diarylethene into its antiparallel diastereomers exhibiting distinct chemical reactivity. A congested parallel diarylethene mechanophore in the (Ra,Sa)-configuration with mirror symmetry is atropisomerized to its antiparallel diastereomers with C2 symmetry under ultrasound-induced force field. The resulting stereochemistry-converted material gains symmetry-allowed reactivity toward conrotatory photocyclization.

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Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers

Abstract

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