Highly Efficient Chirality Transfer from Diamines Encapsulated within a Self-Assembled Calixarene-Salen Host

doi:10.1002/chem.201500333.

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RECERCAT Home > Centres de Recerca de Catalunya (CERCA) > Institut Català d'Investigació Química (ICIQ) > Papers > View document

Use this identifier to quote or link this document: http://hdl.handle.net/2072/356072

dc.contributor.author	Martínez-Rodríguez, Luis
dc.contributor.author	Bandeira, Nuno A. G.
dc.contributor.author	Bo, Carles
dc.contributor.author	Kleij, Arjan W.
dc.date.accessioned	2019-05-22T15:34:22Z
dc.date.available	2019-05-22T15:34:22Z
dc.date.issued	2015-05-04
dc.identifier.uri	http://hdl.handle.net/2072/356072
dc.format.extent	7144 p.
dc.language.iso	eng
dc.rights	L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.source	RECERCAT (Dipòsit de la Recerca de Catalunya)
dc.subject.other	54
dc.title	Highly Efficient Chirality Transfer from Diamines Encapsulated within a Self-Assembled Calixarene-Salen Host
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.embargo.terms	12 mesos
dc.identifier.doi	10.1002/chem.201500333.
dc.rights.accessLevel	info:eu-repo/semantics/openAccess
dc.description.abstract	A calix[4]arene host equipped with two bis-Zn(salphen) complexes self-assembles into a capsular complex in the presence of a chiral diamine guest with an unexpected 2:1 ratio between the host and the guest. Effective chirality transfer from the diamine to the calix- salen hybrid host is observed by CD spectroscopy, and a high stability constant K21 of 1.59  1011 M-2 for the assembled host-guest ensemble has been determined with a substantial cooperativity factor  of 6.4. DFT analysis has been used to investigate the origin of the stability of the host-guest system and the experimental CD spectrum compared with the calculated ones for both possible diastereoisomers showing that the M,M-isomer is the one that is preferentially formed. The current system holds promise for the chirality determination of diamines as evidenced by the investigated substrate scope and the linear relationship between the ee of the diamine and the amplitude of the observed Cotton effects.

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