BIBLIOS

Document type
Journal articles

Document subtype
Full paper

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

Participants in the publication
Luis Martínez-Rodríguez (Author)
Nuno A. G. Bandeira (Author)
BioISI
Carles Bo (Author)
Arjan W. Kleij (Author)

Summary
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 circular dichroism (CD) spectroscopy, and a high stability constant K2,1 of 1.59×1011 M−2 for the assembled host–guest ensemble has been determined with a substantial cooperativity factor α of 6.4. Density functional calculations are used to investigate the origin of the stability of the host–guest system and the experimental CD spectrum compared with those calculated 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.


Where published
Chemistry - A European Journal

Publication Identifiers
ISSN - 0947-6539

Publisher
Wiley



Document Identifiers
DOI - https://doi.org/10.1002/chem.201500333
URL - http://dx.doi.org/10.1002/chem.201500333

Rankings
SCIMAGO Q1 (2020) - 1.687 - Chemistry (miscellaneous)
Web Of Science Q2 (2020) - 5.236 - CHEMISTRY, MULTIDISCIPLINARY - SCIE