Self-assembly of dynamic orthoester cryptates

• Published in: Nature communications Vol. 6; no. 1; p. 7129
• Main Authors: Brachvogel, René-Chris, Hampel, Frank, von Delius, Max
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 22.05.2015; Nature Publishing Group; Nature Pub. Group
• Subjects: 140/131; 639/638/403; 639/638/541/966; 639/638/549; 639/766/530/951; Humanities and Social Sciences; multidisciplinary; Science
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/ncomms8129

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. Cryptands and related molecules are macrocyclic polyethers capable of strongly binding cations. Here, the authors use orthoester exchange for the dynamic one-pot synthesis of crypates, which can bind cations and, given their constitutionally dynamic nature, can also be decomposed to release their guest.