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

[Image: see text] 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...

Descripción completa

Detalles Bibliográficos
Autores principales: Fu, Xuancheng, Zhu, Boyu, Hu, Xiaoran
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10375474/
https://www.ncbi.nlm.nih.gov/pubmed/37413689
http://dx.doi.org/10.1021/jacs.3c03994
_version_ 1785079044467851264
author Fu, Xuancheng
Zhu, Boyu
Hu, Xiaoran
author_facet Fu, Xuancheng
Zhu, Boyu
Hu, Xiaoran
author_sort Fu, Xuancheng
collection PubMed
description [Image: see text] 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 C(2) symmetry under ultrasound-induced force field. The resulting stereochemistry-converted material gains symmetry-allowed reactivity toward conrotatory photocyclization.
format Online
Article
Text
id pubmed-10375474
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-103754742023-07-29 Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers Fu, Xuancheng Zhu, Boyu Hu, Xiaoran J Am Chem Soc [Image: see text] 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 C(2) symmetry under ultrasound-induced force field. The resulting stereochemistry-converted material gains symmetry-allowed reactivity toward conrotatory photocyclization. American Chemical Society 2023-07-06 /pmc/articles/PMC10375474/ /pubmed/37413689 http://dx.doi.org/10.1021/jacs.3c03994 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Fu, Xuancheng
Zhu, Boyu
Hu, Xiaoran
Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers
title Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers
title_full Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers
title_fullStr Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers
title_full_unstemmed Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers
title_short Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers
title_sort force-triggered atropisomerization of a parallel diarylethene to its antiparallel diastereomers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10375474/
https://www.ncbi.nlm.nih.gov/pubmed/37413689
http://dx.doi.org/10.1021/jacs.3c03994
work_keys_str_mv AT fuxuancheng forcetriggeredatropisomerizationofaparalleldiarylethenetoitsantiparalleldiastereomers
AT zhuboyu forcetriggeredatropisomerizationofaparalleldiarylethenetoitsantiparalleldiastereomers
AT huxiaoran forcetriggeredatropisomerizationofaparalleldiarylethenetoitsantiparalleldiastereomers

Ejemplares similares