3D Coumarin Systems Based on [2.2]Paracyclophane Synthesis, Spectroscopic Characterization, and Chiroptical Properties

Marie-Leonie Delcourt 1 Corentin Reynaud 1 Serge Turcaud 1 Ludovic Favereau 2 Jeanne Crassous 2 Laurent Micouin 1 Erica Benedetti 1
1 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques
2 ISCR - Institut des Sciences Chimiques de Rennes
Abstract : In this article, we report the preparation of a series of [2.2]paracyclophane-fused coumarin systems through a simple and general procedure involving a transition-metal-catalyzed cyclization of aryl alkynoates as the key step. We also highlight the influence of the [2.2]paracyclophane (pCp) motif and its "phane" interactions on the spectroscopic properties of the newly synthesized fluorophores, which emit in the blue-green region of the visible spectrum (lambda(em), up to 560 nm) and show extremely large Stokes shifts (up to 230 nm). Finally, we demonstrate that our straightforward approach can easily be used to access optically active planar chiral 3D coumarins. Compared to previously described fluorescent paracyclophanes and other organic dyes, our compact heteroaromatic derivatives show promising chiroptical properties, both in term of circular dichroism (g(abs) similar to 8 x 10(-3)) and circularly polarized luminescence (g(lum) similar to 5 x 10(-3)), thus demonstrating a practical application of our synthetic method.
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UNIV-RENNES1 | UR1-UFR-SPM | ISCR-OMC-PMM | ISCR-OMC | INC-CNRS | UNIV-PARIS5 | UNIV-RENNES | INSA-GROUPE | USPC | ISCR

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Marie-Leonie Delcourt, Corentin Reynaud, Serge Turcaud, Ludovic Favereau, Jeanne Crassous, et al.. 3D Coumarin Systems Based on [2.2]Paracyclophane Synthesis, Spectroscopic Characterization, and Chiroptical Properties. Journal of Organic Chemistry, American Chemical Society, 2019, 84 (2), pp.888-899. ⟨10.1021/acs.joc.8b02773⟩. ⟨hal-02049506⟩

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