title: Self-assembly of dynamic orthoester cryptates.
abstract: The discovery of coronands and cryptands, organic compounds that can accommodate metal ions in a preorganized two- or three-dimensional environment, was a milestone in supramolecular chemistry, leading to countless applications from organic synthesis to metallurgy and medicine. These compounds are typically prepared via multistep organic synthesis and one of their characteristic features is the high stability of their covalent framework. Here we report the use of a dynamic covalent exchange reaction for the one-pot template synthesis of a new class of coronates and cryptates, in which acid-labile O,O,O-orthoesters serve as bridgeheads. In contrast to their classic analogues, the compounds described herein are constitutionally dynamic in the presence of acid and can be induced to release their guest via irreversible deconstruction of the cage. These properties open up a wide range of application opportunities, from systems chemistry to molecular sensing and drug delivery.
authors.affiliation: Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: René-Chris
authors.initials: RC
authors.lastname: Brachvogel
authors.affiliation: Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Hampel
authors.affiliation: Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: Max
authors.identifier: 0000000318522969
authors.initials: M
authors.lastname: von Delius