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Molecular Tweezers: Synthesis and Formation of Host–Guest Complexes

✍ Scribed by Béatrice Legouin; Maud Gayral; Philippe Uriac; Jean-François Cupif; Nicolas Levoin; Loic Toupet; Pierre van de Weghe

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 406 KB
Volume: 2010
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201000729

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✦ Synopsis

Abstract

A chiral molecular tweezer obtained from (+)‐usnic acid placed in solution in the presence of various aromatic compounds afforded complexes with low association constants. Thus, the X‐ray structure of assembly 3i is presented, where the guest is sandwiched between the two pincers of the tweezer. The association constants for various guests were determined through different methods. Finally, other tweezers with electron‐rich aromatic aldehydes and ketones were prepared from (1__R__,2__R__)‐1,2‐diaminocyclohexane. The most interesting complexes were also confirmed through structural analysis, and the best results were obtained with 10‐hydroxyphenanthrene‐9‐carbaldehyde (5i) as the aromatic moiety.

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