YANN FERRAND, University of Bordeaux, France
Aromatic oligomamide capsules as versatile containers for molecular recognition
HOST: Pedro Mateus, LAQV-REQUIMTE - FCT NOVA
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 (Figure 1a). Metal ions can be inserted in the wall of the cavity to enhance binding. Self-assembly can also be used to generate even larger cavity suitable for multiple guests binding (Figure 1b). Recently, we showed that implementing aromatic b sheets in the backbone of these containers allows to create a permanent window that can accelerate guest binding and releasing events (Figure 1c). Finally, photo-switchable aromatic amino acids can be introduced in theses sequences to trigger specific conformational rearrangement of the receptors.
Figure 1. Schematic representations of new architectures based on aromatic oligoamides that can act as receptors: (a) single helical molecular capsule. (b) double helical container. (c) helix-sheet-helix architecture.
 Y. Ferrand, I. Huc Acc. Chem. Res. 2018, 51, 970.
 B. Gole,B. Kauffmann,V. Maurizot,I. Huc, Y. Ferrand Angew. Chem. Int. Ed. 2019, 10.1002/anie.201902378
2017-now: Team leader CBMN, CNRS Researcher (currently Research Director CNRS), UMR5248 CNRS
Subjects: - Biomimetic supramolecular chemistry
- Molecular machines
2007/16: Research Associate (CR CNRS), CBMN, University of Bordeaux, with Prof. I. Huc
2005/07: Post-Doc School of Chemistry, University of Bristol (UK), with Prof. A. P. Davis
2015: Habilitation diploma, Univ. of Bordeaux (France)
2001/05: PhD Thesis, in organic chemistry, at the Univ. of Rennes (France)
1999: Bachelor of Science, in biochemistry, at the Univ. of Rennes (France)
1. Y. Ferrand*, I. Huc* Designing helical molecular capsules based on folded aromatic amide oligomers Acc. Chem. Res. 2018, 51, 970
2. X. Wang, B. Wicher, Y. Ferrand,* I. Huc* Orchestrating directional molecular motions: kinetically controlled supramolecular pathways of a helical host on rodlike guests J. Am. Chem. Soc. 2017, 139, 9350
3. Q. Gan, X. Wang, B. Kauffmann, F. Rosu, Y. Ferrand, I. Huc*. Translation of rod-like template sequences into homochiral assemblies of stacked helical oligomers Nat. Nanotech. 2017, 12, 447–452
4. G. Lautrette, B. Wicher, B. Kauffmann, Y. Ferrand*, I. Huc*. Iterative evolution of an abiotic foldamer sequence for the recognition of guest molecules with atomic precision. J. Am. Chem. Soc. 2016, 138, 10314
5. Y. Ferrand, N. Chandramouli, G. Lautrette, B. Kauffmann, C. D. Mackereth, M. Laguerre, D. Dubreuil, I. Huc*, Iterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose, Nat. Chem. 2015, 7, 334