EventProf. Max von Delius

Self-Assembly of Adaptive Orthoester Architectures

Dynamic covalent chemistry (DCC) is a powerful tool for probing non-covalent interactions, identifying ligands for medicinally relevant biological targets, and for making use of the feature of “error correction” to achieve the synthesis of interesting molecules and materials.

In this talk, I will present our recent work on a previously ignored dynamic covalent reaction: the acid-catalyzed reaction of O,O,O-orthoesters with alcohols (Fig. a),[1] which we were able to use for the one-pot synthesis of cryptates, in which orthoesters act as tripodal bridgeheads.[2] Due to their unique structure (Fig. b), these compounds exhibit a range of unusual properties, including tunable, pH-dependent hydrolysis (Fig. c).[3] Most notably, dynamic orthoester architectures offer an elegant entry to experiments, in which a metal ion selects its preferred host from a dynamic mixture of competing subcomponents (“adaptive host-guest systems”, Fig. d).[4] Of particular relevance to the area of systems chemistry is our recent discovery that ammonium complexes of orthoester cryptands represent the first example of “fluxional supermolecules”, i.e. these host-guest complexes are inherently dynamic and adaptive.[5]

will close the talk by discussing our ongoing work within the ERC-funded project “SUPRANET” towards extending the scope of suitable guest ions and using these compounds in order to facilitate the transport of ions across phospholipid membranes.

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About The Speaker

Max-Von-Delius-portrait

Max von Delius is Professor of Organic Chemistry at the Institute of Organic Chemistry and Advanced Materials of the University of Ulm. He studied chemistry at Friedrich-Alexander University (FAU) in Erlangen  and at Louis-Pasteur University in Strasbourg (France). He obtained his PhD from the University of Edinburgh (Scotland) and was a Leopoldina postdoctoral fellow at the University of Toronto (Canada). In 2018, Max von Delius was awarded the Hoechst Dozentenpreis and from July 2019 his research activities will be supported by the European Research Council (ERC starting grant).

Our research activities are positioned at the interface of supramolecular chemistry, dynamic covalent chemistry and the synthesis of functional materials. One central goal of our group is to study complex chemical networks at equilibrium and beyond (systems chemistry). We are also active in the field of functional organic materials and synthetic carbon allotropes, where we seek to apply the synthesized compounds in new-generation solar cells and photocatalysis.