Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.21/4944
Título: Inherently chiral calix[4]arenes with planar chirality: two new entries to the family
Autor: Prata, José Virgílio Coelho
Barata, Patrícia Alexandra David
Pescitelli, Gennaro
Palavras-chave: Absolute configuration assignment
Chiroptical properties
Planar chirality
TDDFT calculations
Data: Nov-2014
Editora: Walter de Gruyter GMBH
Citação: 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
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.
Peer review: yes
URI: http://hdl.handle.net/10400.21/4944
DOI: 10.1515/pac-2014-0707
ISSN: 0033-4545
Aparece nas colecções:ISEL - Eng. Quim. Biol. - Artigos

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