Chiral Organic Structure-Directing Agents

Chirality is crucial for life. The preparation of enantiopure chiral compounds is highly desirable in the chemical industry, especially in the pharmaceutical sector. In this context, the design of chiral solids able to discriminate between enantiomers of chiral compounds, either during adsorption or...

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Detalles Bibliográficos
Autores: Gómez-Hortigüela Sainz, Luis, Bernardo-Maestro, Beatriz
Tipo de recurso: otro
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/162390
Acceso en línea:http://hdl.handle.net/10261/162390
Access Level:acceso abierto
Palabra clave:Chirality
Zeolites
Templates
Structure-directing agents
Enantiomer
Host-guest chemistry
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spelling Chiral Organic Structure-Directing AgentsGómez-Hortigüela Sainz, LuisBernardo-Maestro, BeatrizChiralityZeolitesTemplatesStructure-directing agentsEnantiomerHost-guest chemistryChirality is crucial for life. The preparation of enantiopure chiral compounds is highly desirable in the chemical industry, especially in the pharmaceutical sector. In this context, the design of chiral solids able to discriminate between enantiomers of chiral compounds, either during adsorption or asymmetric catalytic processes, is one of the greatest challenges nowadays in chemical research. Zeolite-type materials represent ideal candidates to achieve enantioselective chiral solids since they could combine their high stability, surface area, and shape-selectivity with a potential enantioselectivity that could be enhanced by the confinement effect. Despite the occurrence of chiral zeolite frameworks and the strong interest in preparing these chiral solids, very little success has been met in preparing these in homochiral form. The main strategy to induce chirality in zeolite materials has been the use of chiral structure-directing agents, in an attempt to transfer their chiral feature into the nascent zeolite structure. However, although many chiral organic species have directed the crystallization of zeolite frameworks, some of them even being chiral, there is only one unique very recent example of success in transferring the chirality from the organic structure-directing agent into an enantioenriched chiral zeolite material. Chiral coordination compounds have been very successful in transferring their chirality onto inorganic frameworks through the development of extensive H-bond host–guest interactions, but these chiral materials usually collapse upon removal of the guest species. In this chapter we report the different types of chiral molecules, both organic and organometallic compounds, used so far as structure-directing agents in an attempt to promote the crystallization of homochiral zeolites; we analyze in detail the possible reasons for the general failure in transferring their chirality, and we propose approaches to prepare known chiral zeolite frameworks in homochiral form. Furthermore, we also review a different approach we have followed in our group in order to induce chirality in zeolite materials, consisting in the development of chiral spatial distributions of dopants embedded in otherwise achiral zeolite frameworks.Funding from the Spanish Ministry of Science and Innovation (MICINN) through projects MAT2012-31127 and MAT2015-65767-P is acknowledged. BBM acknowledges the Spanish Ministry of Economy and Competitivity for a predoctoral (BES-2013-064605) contract.Peer reviewedSpringer NatureMinisterio de Ciencia e Innovación (España)Ministerio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201820182017info:eu-repo/semantics/otherhttp://purl.org/coar/resource_type/c_3248Postprintinfo:eu-repo/semantics/acceptedVersioninfo:eu-repo/semantics/bookParthttp://hdl.handle.net/10261/162390reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2015-65767-Phttp://dx.doi.org/10.1007/430_2017_9Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1623902026-05-22T06:33:51Z
dc.title.none.fl_str_mv Chiral Organic Structure-Directing Agents
title Chiral Organic Structure-Directing Agents
spellingShingle Chiral Organic Structure-Directing Agents
Gómez-Hortigüela Sainz, Luis
Chirality
Zeolites
Templates
Structure-directing agents
Enantiomer
Host-guest chemistry
title_short Chiral Organic Structure-Directing Agents
title_full Chiral Organic Structure-Directing Agents
title_fullStr Chiral Organic Structure-Directing Agents
title_full_unstemmed Chiral Organic Structure-Directing Agents
title_sort Chiral Organic Structure-Directing Agents
dc.creator.none.fl_str_mv Gómez-Hortigüela Sainz, Luis
Bernardo-Maestro, Beatriz
author Gómez-Hortigüela Sainz, Luis
author_facet Gómez-Hortigüela Sainz, Luis
Bernardo-Maestro, Beatriz
author_role author
author2 Bernardo-Maestro, Beatriz
author2_role author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (España)
Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Chirality
Zeolites
Templates
Structure-directing agents
Enantiomer
Host-guest chemistry
topic Chirality
Zeolites
Templates
Structure-directing agents
Enantiomer
Host-guest chemistry
description Chirality is crucial for life. The preparation of enantiopure chiral compounds is highly desirable in the chemical industry, especially in the pharmaceutical sector. In this context, the design of chiral solids able to discriminate between enantiomers of chiral compounds, either during adsorption or asymmetric catalytic processes, is one of the greatest challenges nowadays in chemical research. Zeolite-type materials represent ideal candidates to achieve enantioselective chiral solids since they could combine their high stability, surface area, and shape-selectivity with a potential enantioselectivity that could be enhanced by the confinement effect. Despite the occurrence of chiral zeolite frameworks and the strong interest in preparing these chiral solids, very little success has been met in preparing these in homochiral form. The main strategy to induce chirality in zeolite materials has been the use of chiral structure-directing agents, in an attempt to transfer their chiral feature into the nascent zeolite structure. However, although many chiral organic species have directed the crystallization of zeolite frameworks, some of them even being chiral, there is only one unique very recent example of success in transferring the chirality from the organic structure-directing agent into an enantioenriched chiral zeolite material. Chiral coordination compounds have been very successful in transferring their chirality onto inorganic frameworks through the development of extensive H-bond host–guest interactions, but these chiral materials usually collapse upon removal of the guest species. In this chapter we report the different types of chiral molecules, both organic and organometallic compounds, used so far as structure-directing agents in an attempt to promote the crystallization of homochiral zeolites; we analyze in detail the possible reasons for the general failure in transferring their chirality, and we propose approaches to prepare known chiral zeolite frameworks in homochiral form. Furthermore, we also review a different approach we have followed in our group in order to induce chirality in zeolite materials, consisting in the development of chiral spatial distributions of dopants embedded in otherwise achiral zeolite frameworks.
publishDate 2017
dc.date.none.fl_str_mv 2017
2018
2018
dc.type.none.fl_str_mv info:eu-repo/semantics/other
http://purl.org/coar/resource_type/c_3248
Postprint
info:eu-repo/semantics/acceptedVersion
dc.type.openaire.fl_str_mv info:eu-repo/semantics/bookPart
format other
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/162390
url http://hdl.handle.net/10261/162390
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2015-65767-P
http://dx.doi.org/10.1007/430_2017_9
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Springer Nature
publisher.none.fl_str_mv Springer Nature
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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