Inherently chiral calix[4]arenes with planar chirality: two new entries to the family

Detalhes bibliográficos
Autor(a) principal: Prata, José Virgílio
Data de Publicação: 2014
Outros Autores: D. Barata, Patrícia, Pescitelli, Gennaro
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.21/4944
Resumo: The synthesis of two new inherently chiral calix[4]arenes (ICCs, 1 and 2), endowed with electron-rich concave surfaces, has been achieved through the desymmetrization of a lower rim distal-bridged oxacyclophane (OCP) macrocycle. The new highly emissive ICCs were resolved by chiral HPLC, and the enantiomeric nature of the isolated antipodes proved by electronic circular dichroism (CD). Using time-dependent density functional calculations of CD spectra, their absolute configurations were established. NMR studies with (S)-Pirkle's alcohol unequivocally showed that the host-guest interactions occur in the chiral pocket comprehending the calix-OCP exo cavities and the carbazole moieties.
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spelling Inherently chiral calix[4]arenes with planar chirality: two new entries to the familyAbsolute configuration assignmentCalix[4]arenesChiroptical propertiesFluorescencePOC-2014Planar chiralityTDDFT calculationsThe synthesis of two new inherently chiral calix[4]arenes (ICCs, 1 and 2), endowed with electron-rich concave surfaces, has been achieved through the desymmetrization of a lower rim distal-bridged oxacyclophane (OCP) macrocycle. The new highly emissive ICCs were resolved by chiral HPLC, and the enantiomeric nature of the isolated antipodes proved by electronic circular dichroism (CD). Using time-dependent density functional calculations of CD spectra, their absolute configurations were established. NMR studies with (S)-Pirkle's alcohol unequivocally showed that the host-guest interactions occur in the chiral pocket comprehending the calix-OCP exo cavities and the carbazole moieties.Walter de Gruyter GMBHRCIPLPrata, José VirgílioD. Barata, PatríciaPescitelli, Gennaro2015-08-24T11:33:19Z2014-112014-11-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.21/4944engPRATA, José Virgílio Coelho; BARATA, Patrícia Alexandra David; PESCITELLI, Gennaro – Inherently chiral Calix[4]Arenes with planar chirality: Two new entries to the family. Pure and Applied Chemistry. ISSN: 0033-4545. Vol. 86, nr. 11 (2014), pp. 1819-18280033-454510.1515/pac-2014-0707metadata only accessinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-08-03T09:47:41ZPortal AgregadorONG
dc.title.none.fl_str_mv Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
title Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
spellingShingle Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
Prata, José Virgílio
Absolute configuration assignment
Calix[4]arenes
Chiroptical properties
Fluorescence
POC-2014
Planar chirality
TDDFT calculations
title_short Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
title_full Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
title_fullStr Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
title_full_unstemmed Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
title_sort Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
author Prata, José Virgílio
author_facet Prata, José Virgílio
D. Barata, Patrícia
Pescitelli, Gennaro
author_role author
author2 D. Barata, Patrícia
Pescitelli, Gennaro
author2_role author
author
dc.contributor.none.fl_str_mv RCIPL
dc.contributor.author.fl_str_mv Prata, José Virgílio
D. Barata, Patrícia
Pescitelli, Gennaro
dc.subject.por.fl_str_mv Absolute configuration assignment
Calix[4]arenes
Chiroptical properties
Fluorescence
POC-2014
Planar chirality
TDDFT calculations
topic Absolute configuration assignment
Calix[4]arenes
Chiroptical properties
Fluorescence
POC-2014
Planar chirality
TDDFT calculations
description The synthesis of two new inherently chiral calix[4]arenes (ICCs, 1 and 2), endowed with electron-rich concave surfaces, has been achieved through the desymmetrization of a lower rim distal-bridged oxacyclophane (OCP) macrocycle. The new highly emissive ICCs were resolved by chiral HPLC, and the enantiomeric nature of the isolated antipodes proved by electronic circular dichroism (CD). Using time-dependent density functional calculations of CD spectra, their absolute configurations were established. NMR studies with (S)-Pirkle's alcohol unequivocally showed that the host-guest interactions occur in the chiral pocket comprehending the calix-OCP exo cavities and the carbazole moieties.
publishDate 2014
dc.date.none.fl_str_mv 2014-11
2014-11-01T00:00:00Z
2015-08-24T11:33:19Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10400.21/4944
url http://hdl.handle.net/10400.21/4944
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv PRATA, José Virgílio Coelho; BARATA, Patrícia Alexandra David; PESCITELLI, Gennaro – Inherently chiral Calix[4]Arenes with planar chirality: Two new entries to the family. Pure and Applied Chemistry. ISSN: 0033-4545. Vol. 86, nr. 11 (2014), pp. 1819-1828
0033-4545
10.1515/pac-2014-0707
dc.rights.driver.fl_str_mv metadata only access
info:eu-repo/semantics/openAccess
rights_invalid_str_mv metadata only access
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Walter de Gruyter GMBH
publisher.none.fl_str_mv Walter de Gruyter GMBH
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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repository.mail.fl_str_mv
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