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Cyclophanes, a bridge between photophysics and supramolecular chemistry

Abstract : In this work and due to their unique electronic properties, 3D-dithia[3.3]paracyclophane-based molecules have been studied for surface nanostructuration applications and as new fluorophore. First, the supramolecular self-assembly of molecules is used to create well-organised 2D-networks on conducting surfaces. However, the use of such substrates tends to quench any electronic properties of the adsorbed molecules. In this context, 3D-dithia[3.3]paracyclophane-based molecules were employed to lift up the active moiety from the surface. In this work, new pyridyl end-capped molecules were designed to self-assemble on any substrate. Preliminary characterisations were performed to study the supramolecular self-assembly of such molecules alone or with co-adsorbers, and the first images of organised 2D-networks on graphite and gold have been obtained by scanning probe microscopy. Second, the design of new and efficient emitter is a hot topic for the fabrication of OLED devices. A new type of compounds is currently investigated for their high electroluminescence efficiency due to thermally activated delayed fluorescence (TADF). This phenomenon is expected from molecules showing low electronic gap between singlet and triplet excited states, which is related to a low overlap of the HOMO and LUMO, localised on the electron-door and acceptor moieties of the molecule, respectively. In this sense, we propose a new design of donor-acceptor molecules where the HOMO (donor) and LUMO (acceptor) are separated by a cyclophane core. We synthesised a couple of emitters and their photophysics properties were studied in solution and in solid state.
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Morgan Auffray. Cyclophanes, a bridge between photophysics and supramolecular chemistry. Material chemistry. Université Pierre et Marie Curie - Paris VI, 2017. English. ⟨NNT : 2017PA066285⟩. ⟨tel-01707788⟩

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