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Transferring axial molecular chirality through a sequence of on-surface reactions

Fine management of chiral processes on solid surfaces has progressed over the years, yet still faces the need for the controlled and selective production of advanced chiral materials. Here, we report on the use of enantiomerically enriched molecular building blocks to demonstrate the transmission of...

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Autores principales: Merino-Díez, Néstor, Mohammed, Mohammed S. G., Castro-Esteban, Jesús, Colazzo, Luciano, Berdonces-Layunta, Alejandro, Lawrence, James, Pascual, J. Ignacio, de Oteyza, Dimas G., Peña, Diego
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159356/
https://www.ncbi.nlm.nih.gov/pubmed/34094071
http://dx.doi.org/10.1039/d0sc01653e
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author Merino-Díez, Néstor
Mohammed, Mohammed S. G.
Castro-Esteban, Jesús
Colazzo, Luciano
Berdonces-Layunta, Alejandro
Lawrence, James
Pascual, J. Ignacio
de Oteyza, Dimas G.
Peña, Diego
author_facet Merino-Díez, Néstor
Mohammed, Mohammed S. G.
Castro-Esteban, Jesús
Colazzo, Luciano
Berdonces-Layunta, Alejandro
Lawrence, James
Pascual, J. Ignacio
de Oteyza, Dimas G.
Peña, Diego
author_sort Merino-Díez, Néstor
collection PubMed
description Fine management of chiral processes on solid surfaces has progressed over the years, yet still faces the need for the controlled and selective production of advanced chiral materials. Here, we report on the use of enantiomerically enriched molecular building blocks to demonstrate the transmission of their intrinsic chirality along a sequence of on-surface reactions. Triggered by thermal annealing, the on-surface reactions induced in this experiment involve firstly the coupling of the chiral reactants into chiral polymers and subsequently their transformation into planar prochiral graphene nanoribbons. Our study reveals that the axial chirality of the reactant is not only transferred to the polymers, but also to the planar chirality of the graphene nanoribbon end products. Such chirality transfer consequently allows, starting from adequate enantioenriched reactants, for the controlled production of chiral and prochiral organic nanoarchitectures with pre-defined handedness.
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spelling pubmed-81593562021-06-04 Transferring axial molecular chirality through a sequence of on-surface reactions Merino-Díez, Néstor Mohammed, Mohammed S. G. Castro-Esteban, Jesús Colazzo, Luciano Berdonces-Layunta, Alejandro Lawrence, James Pascual, J. Ignacio de Oteyza, Dimas G. Peña, Diego Chem Sci Chemistry Fine management of chiral processes on solid surfaces has progressed over the years, yet still faces the need for the controlled and selective production of advanced chiral materials. Here, we report on the use of enantiomerically enriched molecular building blocks to demonstrate the transmission of their intrinsic chirality along a sequence of on-surface reactions. Triggered by thermal annealing, the on-surface reactions induced in this experiment involve firstly the coupling of the chiral reactants into chiral polymers and subsequently their transformation into planar prochiral graphene nanoribbons. Our study reveals that the axial chirality of the reactant is not only transferred to the polymers, but also to the planar chirality of the graphene nanoribbon end products. Such chirality transfer consequently allows, starting from adequate enantioenriched reactants, for the controlled production of chiral and prochiral organic nanoarchitectures with pre-defined handedness. The Royal Society of Chemistry 2020-04-29 /pmc/articles/PMC8159356/ /pubmed/34094071 http://dx.doi.org/10.1039/d0sc01653e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Merino-Díez, Néstor
Mohammed, Mohammed S. G.
Castro-Esteban, Jesús
Colazzo, Luciano
Berdonces-Layunta, Alejandro
Lawrence, James
Pascual, J. Ignacio
de Oteyza, Dimas G.
Peña, Diego
Transferring axial molecular chirality through a sequence of on-surface reactions
title Transferring axial molecular chirality through a sequence of on-surface reactions
title_full Transferring axial molecular chirality through a sequence of on-surface reactions
title_fullStr Transferring axial molecular chirality through a sequence of on-surface reactions
title_full_unstemmed Transferring axial molecular chirality through a sequence of on-surface reactions
title_short Transferring axial molecular chirality through a sequence of on-surface reactions
title_sort transferring axial molecular chirality through a sequence of on-surface reactions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159356/
https://www.ncbi.nlm.nih.gov/pubmed/34094071
http://dx.doi.org/10.1039/d0sc01653e
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