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Chirality induction from a chiral guest to the hydrogen bonding network of its hexameric resorcinarene host capsule

Pollok, Corina H. and Zhang, Qi and Tiefenbacher, Konrad and Merten, Christian. (2017) Chirality induction from a chiral guest to the hydrogen bonding network of its hexameric resorcinarene host capsule. ChemPhysChem, 18 (15). pp. 1987-1991.

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Official URL: http://edoc.unibas.ch/58969/

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Abstract

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.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Synthesis of Functional Modules (Tiefenbacher)
UniBasel Contributors:Tiefenbacher, Konrad Karl and Zhang, Qi
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:1439-4235
e-ISSN:1439-7641
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:22 Jan 2018 13:11
Deposited On:22 Jan 2018 13:11

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