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

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  • Georgios Charalambidis

    (Bioinorganic Chemistry Laboratory, University of Crete)

  • Evangelos Georgilis

    (University of Crete, Vassilika Vouton
    Institute of Electronic Structure and Laser (I.E.S.L.) Foundation for Research and Technology Hellas (FO.R.T.H.) Vassilika Vouton)

  • Manas K. Panda

    (Bioinorganic Chemistry Laboratory, University of Crete
    Present address: CSIR-NIIST, Trivandrum, India)

  • Christopher E. Anson

    (Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry)

  • Annie K. Powell

    (Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry
    Karlsruhe Institute of Technology (KIT), Institute for Nanotechnology (INT))

  • 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
    Present address: abcr GmbH, Im Schlehert 10, 76187 Karlsruhe, Germany)

  • 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
    Swedish e-Science Research Centre (SeRC), 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
    Institute of Electronic Structure and Laser (I.E.S.L.) Foundation for Research and Technology Hellas (FO.R.T.H.) 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)

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.

Suggested Citation

  • 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, 2016. "A switchable self-assembling and disassembling chiral system based on a porphyrin-substituted phenylalanine–phenylalanine motif," Nature Communications, Nature, vol. 7(1), pages 1-11, November.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms12657
    DOI: 10.1038/ncomms12657
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    Cited by:

    1. Alaa A. Zaky & Ahmed Fathy & Hegazy Rezk & Konstantina Gkini & Polycarpos Falaras & Amlak Abaza, 2021. "A Modified Triple-Diode Model Parameters Identification for Perovskite Solar Cells via Nature-Inspired Search Optimization Algorithms," Sustainability, MDPI, vol. 13(23), pages 1-22, November.

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