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Mechanofluorochromism of pyrene-derived amidophosphonates

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Abstract

Aiming to develop a library of organic mechanofluorochromic (MFC) materials, solid-state emission properties of pyrene-derivatives with amidophosphonate groups (diethyl 1-(pyrene-1-carboxamido)alkylphosphonates, alkyl: methyl, isopropyl, phenyl) were investigated. All of these compounds were found to show strong blue fluorescence, and blue-to-green emission shift was identified upon grinding. Monomer and several excimer emissive species were identified by steady-state and time-resolved fluorescence nvestigations. The characteristic green-to-blue thermal back reaction was observed even at room temperature without additives, which would be related to the flexibility of side groups for molecular rearrangement. We here demonstrated that the pyrene-derived compounds can be attractive platforms to host MFC properties.

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Authors and Affiliations

  1. Université Paris-Saclay, ENS Paris-Saclay, CNRS, PPSM, 94235, Cachan, France

    Yuichi Hirai, Arnaud Brosseau, Rémi Métivier & Clémence Allain

  2. Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403, Łódź, Poland

    Anna Wrona-Piotrowicz & Janusz Zakrzewski

  3. Université Paris-Saclay, CNRS, ICMMO, 91405, Orsay, France

    Régis Guillot

Authors
  1. Yuichi Hirai
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  2. Anna Wrona-Piotrowicz
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  3. Janusz Zakrzewski
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  4. Arnaud Brosseau
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  5. Régis Guillot
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  6. Rémi Métivier
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  7. Clémence Allain
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Corresponding author

Correspondence to Rémi Métivier.

Additional information

Electronic supplementary information (ESI) available: Spectroscopic data in solution and in the solid state. CCDC 1973249-1973251. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9pp00457b

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Hirai, Y., Wrona-Piotrowicz, A., Zakrzewski, J. et al. Mechanofluorochromism of pyrene-derived amidophosphonates. Photochem Photobiol Sci 19, 229–234 (2020). https://doi.org/10.1039/c9pp00457b

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  • DOI: https://doi.org/10.1039/c9pp00457b

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