Absolute configuration and host-guest binding of chiral porphyrin-cages by a combined chiroptical and theoretical approach

Jiangkun Ouyang, Anne Swartjes, Marc Geerts, Pieter J. Gilissen, Danni Wang, Paula C. P. Teeuwen, Paul Tinnemans, Nicolas Vanthuyne, Sara Chentouf, Floris P. J. T. Rutjes, Jean-Valère Naubron (), Jeanne Crassous (), Johannes A. A. W. Elemans () and Roeland J. M. Nolte ()
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Jiangkun Ouyang: Radboud University, Institute for Molecules and Materials
Anne Swartjes: Radboud University, Institute for Molecules and Materials
Marc Geerts: Radboud University, Institute for Molecules and Materials
Pieter J. Gilissen: Radboud University, Institute for Molecules and Materials
Danni Wang: Radboud University, Institute for Molecules and Materials
Paula C. P. Teeuwen: Radboud University, Institute for Molecules and Materials
Paul Tinnemans: Radboud University, Institute for Molecules and Materials
Nicolas Vanthuyne: Aix Marseille Univ, CNRS, Centrale Marseille, iSm2
Sara Chentouf: FSCM - Spectropole, FR1739, Aix-Marseille University, CNRS, Centrale Marseille
Floris P. J. T. Rutjes: Radboud University, Institute for Molecules and Materials
Jean-Valère Naubron: FSCM - Spectropole, FR1739, Aix-Marseille University, CNRS, Centrale Marseille
Jeanne Crassous: Univ Rennes, CNRS, Institut des Sciences Chimiques de Rennes, ISCR-UMR 6226
Johannes A. A. W. Elemans: Radboud University, Institute for Molecules and Materials
Roeland J. M. Nolte: Radboud University, Institute for Molecules and Materials

Nature Communications, 2020, vol. 11, issue 1, 1-11

Abstract: Abstract Porphyrin cage-compounds are used as biomimetic models and substrate-selective catalysts in supramolecular chemistry. In this work we present the resolution of planar-chiral porphyrin cages and the determination of their absolute configuration by vibrational circular dichroism in combination with density functional theory calculations. The chiral porphyrin-cages form complexes with achiral and chiral viologen-guests and upon binding one of the axial enantiomorphs of the guest is bound selectively, as is indicated by induced-electronic-dichroism-spectra in combination with calculations. This host-guest binding also leads to unusual enhanced vibrational circular dichroism, which is the result of a combination of phenomena, such as rigidification of the host and guest structures, charge transfer, and coupling of specific vibration modes of the host and guest. The results offer insights in how the porphyrin cage-compounds may be used to construct a future molecular Turing machine that can write chiral information onto polymer chains.

Date: 2020
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DOI: 10.1038/s41467-020-18596-1

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