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A molecular propeller effect for chiral separation and analysis

Enantiomers share nearly identical physical properties but have different chiral geometries, making their identification and separation difficult. Here we show that when exposed to a rotating electric field, the left- and right-handed chiral molecules rotate with the field and act as microscopic pro...

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Detalles Bibliográficos
Autores principales: Clemens, Jonathon B., Kibar, Osman, Chachisvilis, Mirianas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Pub. Group 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4525176/
https://www.ncbi.nlm.nih.gov/pubmed/26216219
http://dx.doi.org/10.1038/ncomms8868
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author Clemens, Jonathon B.
Kibar, Osman
Chachisvilis, Mirianas
author_facet Clemens, Jonathon B.
Kibar, Osman
Chachisvilis, Mirianas
author_sort Clemens, Jonathon B.
collection PubMed
description Enantiomers share nearly identical physical properties but have different chiral geometries, making their identification and separation difficult. Here we show that when exposed to a rotating electric field, the left- and right-handed chiral molecules rotate with the field and act as microscopic propellers; moreover, owing to their opposite handedness, they propel along the axis of field rotation in opposite directions. We introduce a new molecular parameter called hydrodynamic chirality to characterize the coupling of rotational motion of a chiral molecule into its translational motion and quantify the direction and velocity of such motion. We demonstrate >80% enrichment level of counterpart enantiomers in solution without using chiral selectors or circularly polarized light. We expect our results to have an impact on multiple applications in drug discovery, analytical and chiral chemistry, including determination of absolute configuration, as well as in influencing the understanding of artificial and natural molecular systems where rotational motion of the molecules is involved.
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spelling pubmed-45251762015-09-04 A molecular propeller effect for chiral separation and analysis Clemens, Jonathon B. Kibar, Osman Chachisvilis, Mirianas Nat Commun Article Enantiomers share nearly identical physical properties but have different chiral geometries, making their identification and separation difficult. Here we show that when exposed to a rotating electric field, the left- and right-handed chiral molecules rotate with the field and act as microscopic propellers; moreover, owing to their opposite handedness, they propel along the axis of field rotation in opposite directions. We introduce a new molecular parameter called hydrodynamic chirality to characterize the coupling of rotational motion of a chiral molecule into its translational motion and quantify the direction and velocity of such motion. We demonstrate >80% enrichment level of counterpart enantiomers in solution without using chiral selectors or circularly polarized light. We expect our results to have an impact on multiple applications in drug discovery, analytical and chiral chemistry, including determination of absolute configuration, as well as in influencing the understanding of artificial and natural molecular systems where rotational motion of the molecules is involved. Nature Pub. Group 2015-07-28 /pmc/articles/PMC4525176/ /pubmed/26216219 http://dx.doi.org/10.1038/ncomms8868 Text en Copyright © 2015, Nature Publishing Group, a division of Macmillan Publishers Limited. All Rights Reserved. http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Clemens, Jonathon B.
Kibar, Osman
Chachisvilis, Mirianas
A molecular propeller effect for chiral separation and analysis
title A molecular propeller effect for chiral separation and analysis
title_full A molecular propeller effect for chiral separation and analysis
title_fullStr A molecular propeller effect for chiral separation and analysis
title_full_unstemmed A molecular propeller effect for chiral separation and analysis
title_short A molecular propeller effect for chiral separation and analysis
title_sort molecular propeller effect for chiral separation and analysis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4525176/
https://www.ncbi.nlm.nih.gov/pubmed/26216219
http://dx.doi.org/10.1038/ncomms8868
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