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Chirality Induction from a Chiral Guest to the Hydrogen‐Bonding Network of Its Hexameric Resorcinarene Host Capsule
Author(s) -
Pollok Corina H.,
Zhang Qi,
Tiefenbacher Konrad,
Merten Christian
Publication year - 2017
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201700610
Subject(s) - circular dichroism , chemistry , resorcinarene , chirality (physics) , steric effects , supramolecular chemistry , molecule , stereochemistry , hydrogen bond , amine gas treating , supramolecular chirality , crystallography , capsule , organic chemistry , chiral symmetry , nambu–jona lasinio model , quark , physics , quantum mechanics , botany , biology
The hexameric capsule of resorcin[4]arene 1 is capable of encapsulating tertiary amines, which has recently been used in the application of [( 1 ) 6 (H 2 O) 8 ] as (co‐)catalyst in various asymmetric reactions. However, not much is known about the highly asymmetric but conformationally very dynamic structure of the capsule after uptake of chiral molecules. Therefore, in this contribution, we utilize electronic circular dichroism and vibrational circular dichroism spectroscopy to investigate how several chiral guest molecules affect the structural preferences of the capsule [( 1 ) 6 (H 2 O) 8 ]. In particular, we show that one small chiral amine encapsulated in [( 1 ) 6 (H 2 O) 8 ] is sufficient to control and dictate the stereochemical preferences of the entire capsule. Furthermore, neither strong π–π interactions nor a significant steric bulk are required for this induction. The observation of such a chiral imprint of the guest's stereochemistry onto its host molecule is expected to have implications also for other supramolecular capsules.