A switchable self-assembling and disassembling chiral system based on a porphyrin-substituted phenylalanine–phenylalanine motif

Georgios Charalambidis, Evangelos Georgilis, Manas K. Panda, Christopher E. Anson, Annie K. Powell, Stephen Doyle, David Moss, Tobias Jochum, Peter N. Horton, Simon J. Coles, Mathieu Linares, David Beljonne, Jean-Valère Naubron, Jonas Conradt, Heinz Kalt, Anna Mitraki (), Athanassios G. Coutsolelos () and Teodor Silviu Balaban ()
Additional contact information
Georgios Charalambidis: Bioinorganic Chemistry Laboratory, University of Crete
Evangelos Georgilis: University of Crete, Vassilika Vouton
Manas K. Panda: Bioinorganic Chemistry Laboratory, University of Crete
Christopher E. Anson: Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry
Annie K. Powell: Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry
Stephen Doyle: Karlsruhe Institute of Technology, Institute for Synchrotron Radiation and ANKA
David Moss: Karlsruhe Institute of Technology, Institute for Synchrotron Radiation and ANKA
Tobias Jochum: Karlsruhe Institute of Technology, Institute for Synchrotron Radiation and ANKA
Peter N. Horton: School of Chemistry, EPSRC National Crystallography Service, University of Southampton
Simon J. Coles: School of Chemistry, EPSRC National Crystallography Service, University of Southampton
Mathieu Linares: Chemistry and Biology, Linköping University
David Beljonne: Chimie des Matériaux Nouveaux and Centre d'Innovation et de Recherche en Matériaux Polymères, Université de Mons—UMONS/Materia Nova
Jean-Valère Naubron: Aix Marseille Université, CNRS FR 1739, Spectropole, Avenue Escadrille Normandie Niemen
Jonas Conradt: Karlsruhe Institute of Technology (KIT), Institute of Applied Physics and Center for Functional Nanostructures (CFN)
Heinz Kalt: Karlsruhe Institute of Technology (KIT), Institute of Applied Physics and Center for Functional Nanostructures (CFN)
Anna Mitraki: University of Crete, Vassilika Vouton
Athanassios G. Coutsolelos: Bioinorganic Chemistry Laboratory, University of Crete
Teodor Silviu Balaban: Aix Marseille Univ, CNRS, Centrale Marseille, Institut des Sciences Moléculaires de Marseille (iSm2), UMR 7313, Chirosciences, Avenue Escadrille Normandie Niemen

Nature Communications, 2016, vol. 7, issue 1, 1-11

Abstract: Abstract Artificial light-harvesting systems have until now not been able to self-assemble into structures with a large photon capture cross-section that upon a stimulus reversibly can switch into an inactive state. Here we describe a simple and robust FLFL-dipeptide construct to which a meso-tetraphenylporphyrin has been appended and which self-assembles to fibrils, platelets or nanospheres depending on the solvent composition. The fibrils, functioning as quenched antennas, give intense excitonic couplets in the electronic circular dichroism spectra which are mirror imaged if the unnatural FDFD-analogue is used. By slightly increasing the solvent polarity, these light-harvesting fibres disassemble to spherical structures with silent electronic circular dichroism spectra but which fluoresce. Upon further dilution with the nonpolar solvent, the intense Cotton effects are recovered, thus proving a reversible switching. A single crystal X-ray structure shows a head-to-head arrangement of porphyrins that explains both their excitonic coupling and quenched fluorescence.

Date: 2016
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DOI: 10.1038/ncomms12657

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