Control of Dynamic Chirality in Donor-Acceptor Fluorophores.

Autor: Coehlo M; Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Gif-sur-Yvette, F-91191, France., Frédéric L; Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Gif-sur-Yvette, F-91191, France.; Université Paris-Saclay, ENS Paris-Saclay, CNRS, PPSM, Gif-sur-Yvette, F-91190, France., Poulard L; Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Gif-sur-Yvette, F-91191, France., Ferdi N; Aix Marseille Univ, CNRS, Centrale Med, FSCM, Marseille, France., Estaque L; Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Gif-sur-Yvette, F-91191, France., Desmarchelier A; Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Gif-sur-Yvette, F-91191, France., Clavier G; Université Paris-Saclay, ENS Paris-Saclay, CNRS, PPSM, Gif-sur-Yvette, F-91190, France., Dognon JP; Université Paris-Saclay, CEA, CNRS, NIMBE, Gif-sur-Yvette, 91191, France., Favereau L; Université de Rennes, CNRS ISCR-UMR 6226, Rennes, 35042, France., Giorgi M; Aix Marseille Univ, CNRS, Centrale Med, FSCM, Marseille, France., Naubron JV; Aix Marseille Univ, CNRS, Centrale Med, FSCM, Marseille, France., Pieters G; Université Paris-Saclay, CEA, INRAE, Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Gif-sur-Yvette, F-91191, France.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Sep 17, pp. e202414490. Date of Electronic Publication: 2024 Sep 17.
DOI: 10.1002/anie.202414490
Abstrakt: Recently, the control of dynamic chirality has emerged as a powerful strategy to design chiral functional materials. In this context, we describe herein a molecular design in which a tethered configurationally stable binaphthyl chiral unit efficiently controls the dynamic chirality of donor-acceptor fluorophores, involving diverse indolocarbazoles as electron donors and terephthalonitrile as an electron acceptor. The high conformational discrimination in such a molecular system suggested by density functional theory calculations is experimentally probed using electronic and vibrational circular dichroism and confirmed by the crystallization of these chiral molecules in gel and their single crystal X-ray diffraction analysis. This work also highlights the positive effect of the configurationally stable chiral unit on the magnitude of the dissymmetry factors of the active dynamically chiral fluorophores, both in ground and excited states, through chiral perturbation.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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