[SEMINAR] From Molecular Recognition to Catalysis

Title: From Molecular Recognition to Catalysis: Designing an Artificial Decarboxylase

Speaker: Yann Ferrand (yann.ferrand@u-bordeaux.fr)

From: Université de Bordeaux, CNRS CBMN UMR 5248 

Abstract: Aromatic oligoamides present all the required features to act as efficient scaffolds for the molecular recognition of chiral polar guests. Their oligomeric nature offers unmatched modularity in that each and every monomer may be varied in order to tune the structure, the dynamics and host-guest properties. Helices with variable inner diameters can be used as capsules that can totally isolate a substrate from the external medium. While catalysis using foldamers is a rapidly developing area, there has been no account on catalysis within foldamer containers making use of their recognition properties.

Recent efforts in our group have focused on the design of capsule shaped catalysts for the decarboxylations of perfluorosuccinic acid. The functionalization of a capsule with electron donating morpholine moieties allowed the deprotonation of the dicarboxylic acid guest and its subsequent double decarboxylations. Surprisingly, the CO2 molecules generated during the reaction could be trapped in the foldamer cavity and the resulting gas-foldamer complex could be characterized in solution and in the solid state. Alternatively, heating of the capsule in the presence of an excess of diacid allows for catalysis to proceed.

References

[1] Y. Ferrand et al, J. Am. Chem. Soc. 2010, 132, 7858.

[2] P. Mateus et al, Chem. Sci. 2021, 12, 3743.