The Dynamic Chemistry of Orthoesters
23rd IUPAC Conference on Physical Organic Chemistry (ICPOC23) 3rd – 8th July 2016 • Sydney • Australia
The Dynamic Chemistry of Orthoesters M. von Delius,a,* a
Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg (FAU), 91054 Erlangen, Germany *[email protected]
Dynamic covalent chemistry (DCC) has developed into a powerful tool for probing non-covalent interactions, identifying ligands for medicinally relevant biotargets, and for making use of the feature of “error correction” for the synthesis of interesting molecules, (porous) materials, gels and polymers.1 In this talk, I will present studies during which we established the reversible reaction of orthoesters with alcohols as a new tool for the field of DCC.2 We were able to use this process for the self-assembly of cryptates, in which O,O,O-orthoesters act as bridgeheads.3 Due to their unique structure (see Figure), these compounds exhibit a range of unusual properties4 and preliminary studies point towards a broad scope of the self-assembly process. The dynamic chemistry of orthoesters also offers the unprecedented prospect of a dynamic combinatorial identification of particularly stable metal/cryptand pairs from mixtures of subcomponents (“adaptive host/guest systems”).5 Finally, I will discuss possible applications of orthoester cryptates, as well as ongoing projects on related orthoester architectures.
References 1. 2. 3. 4. 5.
Jin, Y.; Yu, C.; Denman, R. J; Zhang, W. Chem. Soc. Rev. 2013, 42, 6634-6654. R.-C. Brachvogel, M. von Delius, Chem. Sci. 2015, 6, 1399-1402. R.-C. Brachvogel, F. Hampel, M. von Delius, Nature Commun. 2015, 6, 7129. R.-C. Brachvogel, H. Maid, M. von Delius, Int. J. Mol. Sci. 2015, 16, 20641-20656. O. Shyshov, R.-C. Brachvogel, M. von Delius, in preparation.
ILC20
The Dynamic Chemistry of Orthoesters M. von Delius,a,* a
Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg (FAU), 91054 Erlangen, Germany *[email protected]
Dynamic covalent chemistry (DCC) has developed into a powerful tool for probing non-covalent interactions, identifying ligands for medicinally relevant biotargets, and for making use of the feature of “error correction” for the synthesis of interesting molecules, (porous) materials, gels and polymers.1 In this talk, I will present studies during which we established the reversible reaction of orthoesters with alcohols as a new tool for the field of DCC.2 We were able to use this process for the self-assembly of cryptates, in which O,O,O-orthoesters act as bridgeheads.3 Due to their unique structure (see Figure), these compounds exhibit a range of unusual properties4 and preliminary studies point towards a broad scope of the self-assembly process. The dynamic chemistry of orthoesters also offers the unprecedented prospect of a dynamic combinatorial identification of particularly stable metal/cryptand pairs from mixtures of subcomponents (“adaptive host/guest systems”).5 Finally, I will discuss possible applications of orthoester cryptates, as well as ongoing projects on related orthoester architectures.
References 1. 2. 3. 4. 5.
Jin, Y.; Yu, C.; Denman, R. J; Zhang, W. Chem. Soc. Rev. 2013, 42, 6634-6654. R.-C. Brachvogel, M. von Delius, Chem. Sci. 2015, 6, 1399-1402. R.-C. Brachvogel, F. Hampel, M. von Delius, Nature Commun. 2015, 6, 7129. R.-C. Brachvogel, H. Maid, M. von Delius, Int. J. Mol. Sci. 2015, 16, 20641-20656. O. Shyshov, R.-C. Brachvogel, M. von Delius, in preparation.
ILC20
