Synthesis of Functional Modules

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.

The new PI Konrad Tiefenbacher was recently appointed assistant professor by the University of Basel. He started his research for the NCCR Molecular Systems Engineering in the field of synthesis of functional modules on 1 June 2016. > more

Articles

Q. Zhang, L. Catti, K. TiefenbacherCatalysis inside the Hexameric Resorcinarene Capsule“  (2018). [Link]
Q. Zhang, J. Rinkel, B. Goldfuss, J. S. Dickschat, K. TiefenbacherSesquiterpene cyclizations catalysed inside the resorcinarene capsule and application in the short synthesis of isolongifolene and isolongifolenone“ Nat. Catal. (2018). [Link]
J. M. Köster, K. TiefenbacherElucidating the Importance of Hydrochloric Acid as a Cocatalyst for Resorcinarene‐Capsule‐Catalyzed Reactions“ ChemCatChem (2018). [Link]
T. Braeuer, Q. Zhang, K. TiefenbacherIminium Catalysis inside a Self-Assembled Supramolecular Capsule: Scope and Mechanistic Studies“ J. Am. Chem. Soc. (2017). [Link]
Q. Zhang, L. Catti, J. Pleiss, K. TiefenbacherTerpene Cyclizations inside a Supramolecular Catalyst: Leaving Group-Controlled Product Selectivity and Mechanistic Studies“ J. Am. Chem. Soc. (2017). [Link]
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). [Link]
L. Catti, A. Pöthig, K. TiefenbacherHost-Catalyzed Cyclodehydration–Rearrangement Cascade Reaction of Unsaturated Tertiary Alcohols“ Adv. Synth. Catal. 359, 1331-38 (2017). [Link]
Q. Zhang, L. Catti, V. R. I. Kaila, K. TiefenbacherTo catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene“ Chem. Sci. (2017). [Link]

Project Leader

Konrad Tiefenbacher

Collaborations

In collaboration with the project lead by Stefan Matile, the construction of novel water-soluble nano-reaction chambers will be investigated. Spatial segregation of nano-reaction chambers will be performed in collaboration with projects led by Wolfgang Meier and Cornelia G. Palivan. The exploration of multi-catalyst tandem reactions will involve collaborations with projects led by Thomas R. Ward and Stefan Matile

Lab

Read more about the Tiefenbacher-Group here.