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Tackling Current Limitations of the Supramolecular Resorcinarene Capsule Catalyst: Compatibility with Water, Size, and Anionic Reactions

Applicant Tiefenbacher Konrad
Number 178714
Funding scheme Project funding (Div. I-III)
Research institution Departement Chemie Universität Basel
Institution of higher education University of Basel - BS
Main discipline Organic Chemistry
Start/End 01.05.2018 - 30.04.2022
Approved amount 822'150.00
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Keywords (3)

Supramolecular chemistry; Catalysis; Enzymes

Lay Summary (German)

Dieses Forschungsvorhaben beschäftigt sich mit der Nachahmung natürlicher Enzyme mittels neuartiger künstlicher Strukturen. Enzyme sind Katalysatoren, also Reaktionsbeschleuniger, die in der Natur und auch im menschlichen Körper den Grossteil aller Reaktionen stark beeinflussen.
Lay summary

Ein Ziel des Projekts ist die Entwicklung eines künstlichen enzymartigen Katalysators, der mit Wasser kompatibel ist. Dies ist wichtig, da dadurch eine Vielzahl an vergleichenden Studien mit natürlichen Enzymen ermöglicht wird. Im zweiten und dritten Teil des Vorhabens beschäftigen wir uns mit der Entwicklung neuer Katalysatoren, die es uns ermöglichen sollten Reaktionen zu beeinflussen, die bisher nicht beziehungsweise nur unzureichend kontrolliert werden konnten. Langfristig erwarten wir uns, dass unsere Arbeiten an enzymartigen Katalysatoren Verbesserungen bei der chemischen Produktion von Wirkstoffen ermöglichen.

Direct link to Lay Summary Last update: 11.04.2018

Responsible applicant and co-applicants



Chemists have been inspired by natural enzymes since their discovery. The ability to perform catalysis inside small defined cavities is intriguing and offers possibilities to overcome selectivity issues observed in regular solution experiments. Supramolecular capsules offer one way to mimic the basic working principle of enzymes to some extent. Interestingly, only two supramolecular capsules have seen use in a wider range of different reactions so far. The hexameric resorcinarene capsule is one of them and it has been investigated intensively in my group over the last years.In this proposal, we aim at overcoming three fundamental limitations of the resorcinarene-based capsule:1. Since the capsule is held together via hydrogen bonds, it is incompatible with large excess of polar molecules (for instance large excess of polar substrate or solvent). Especially limiting is the incompatibility with aqueous solvents, which impedes multicatalyst tandem reactions with natural enzymes. We will construct covalently linked analogs of similar dimensions. Due to the attached ethylene glycol residues, they will be soluble in aqueous media.2. The limited volume impedes exciting studies of encapsulated gold(I) or iminium-based catalysts. Several unusually large hydrogen bond-based capsules will be developed. They will be based on novel large calixarene building blocks, which remained completely unexplored so far.3. Catalysis inside capsules is mainly limited to reactions with cationic intermediates and transition states so far. No capsule catalyst is available for anionic reactions. Novel host systems will be synthesized which contain pi-acidic walls. Since these hosts can engage with the anionic intermediates/transition states from several sides, we anticipate increased and altered reactivity as compared to the acyclic systems known.Research into catalysis inside supramolecular capsules is still in its infancy. Therefore, it is important to overcome current limitations, to be able to explore the potential of this exciting area in catalysis. We are confident that the research proposed herein is well suited to achieve these goals.