Synthesis of Functional Modules - NCCR MSE

Synthesis of Functional Modules

We are creating and exploring nano-reaction chambers as catalysts for substrate and product selective reactions. Such functional modules will be the basis for the construction of molecular factories.

The successful creation of a molecular factory relies on the delicate interplay of all its subcomponents. To avoid undesired cross-reactivity, the subcomponents have to display high substrate selectivity. One way to achieve substrate selectivity is the utilization of nano-reaction chambers, which due to their limited cavity volume only convert molecules of suitable size.

Beside substrate selectivity, nano-reaction chambers also provide product selectivity. Due to the restricted environment inside the catalyst, the substrate conformation is influenced, which can lead to different products than in a regular solution experiment. Additionally, weak interactions between the host and the guest molecule can influence the reaction pathway.

As a first step towards molecular factories, we will investigate multi-catalyst tandem reactions utilizing two or more nano-reaction chambers. Natural enzymes will be combined with man-made nano-reaction chambers to obtain novel reactivity.

Publications

Q. Zhang, L. Catti, K. Tiefenbacher “Catalysis inside the Hexameric Resorcinarene Capsule“ Acc. Chem. Res. 2018. [DOI]
Q. Zhang, J. Rinkel, B. Goldfuss, J. S. Dickschat, K. Tiefenbacher “Sesquiterpene cyclizations catalysed inside the resorcinarene capsule and application in the short synthesis of isolongifolene and isolongifolenone“ Nat. Catal. 2018. [DOI]
J. M. Köster, K. Tiefenbacher “Elucidating the Importance of Hydrochloric Acid as a Cocatalyst for Resorcinarene‐Capsule‐Catalyzed Reactions“ ChemCatChem 2018. [DOI]
T. Braeuer, Q. Zhang, K. Tiefenbacher “Iminium Catalysis inside a Self-Assembled Supramolecular Capsule: Scope and Mechanistic Studies“ J. Am. Chem. Soc. 2017. [DOI]
Q. Zhang, L. Catti, J. Pleiss, K. Tiefenbacher “Terpene Cyclizations inside a Supramolecular Catalyst: Leaving Group-Controlled Product Selectivity and Mechanistic Studies“ J. Am. Chem. Soc. 2017. [DOI]
C. H. Pollok, Q. Zhang, K. Tiefenbacher, C. Merten “Chirality induction from a chiral guest to the hydrogen bonding network of its hexameric resorcinarene host capsule“ ChemPhysChem 2017. [DOI]
L. Catti, A. Pöthig, K. Tiefenbacher “Host-Catalyzed Cyclodehydration–Rearrangement Cascade Reaction of Unsaturated Tertiary Alcohols“ Adv. Synth. Catal. 2017, 359:1331-38. [DOI]
Q. Zhang, L. Catti, V. R. I. Kaila, K. Tiefenbacher “To catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene“ Chem. Sci. 2017. [DOI]