Light-responsive pyrazine-based systems: probing aromatic diarylethene photocyclization
| Autor: | Jovana V. Milić, Renana Gershoni-Poranne, Cédric Schaack, Nora Hellou, Jeanne Crassous, Corinne Boudon, Nils Trapp, Florin Isenrich, Georg Gescheidt, Dmytro Neshchadin, Laurent Ruhlmann, François Diederich, Sylvain Egloff |
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| Přispěvatelé: | Eidgenössische Technische Hochschule - Swiss Federal Institute of Technology [Zürich] (ETH Zürich), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Graz University of Technology [Graz] (TU Graz), Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Swiss National Science Foundation [200020_159802], Agence National de la Recherche Fund [12-BS07-0004-METALHEL-01], ANR-12-BS07-0004,MetalHel,Dérivés hélicéniques multifonctionnels à base de métaux(2012), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Pyrazine
010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Aromaticity 010402 general chemistry Photochemistry 01 natural sciences 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry.chemical_compound Photochromism General Energy Quinoxaline Helicene chemistry Diarylethene Ultrafast laser spectroscopy Density functional theory Physical and Theoretical Chemistry |
| Zdroj: | The Journal of Physical Chemistry C, 122 (33) Journal of Physical Chemistry C Journal of Physical Chemistry C, American Chemical Society, 2018, 122 (33), pp.19100-19109. ⟨10.1021/acs.jpcc.8b05019⟩ Journal of Physical Chemistry C, 2018, 122 (33), pp.19100-19109. ⟨10.1021/acs.jpcc.8b05019⟩ |
| ISSN: | 1932-7447 1932-7455 |
| DOI: | 10.1021/acs.jpcc.8b05019⟩ |
| Popis: | International audience; Here, we present an investigation of the photocyclization of novel aromatic diarylethene (DAE) systems 1-3 based on pyrazine, quinoxaline, and helicene scaffolds. These prospective photoswitches were designed using density functional theory calculations and analyzed in solution and in the solid state by cyclic and rotating disk voltammetry, UV-vis and transient absorption spectroscopy, as well as X-ray crystallography. Additionally, nucleus-independent chemical shift calculations were performed to investigate the influence of aromaticity on the photocyclization ability. While pyrazine-2,3-diyl-extended DAE system 1 demonstrated photoswitching ability with short lifetimes of the cyclized form, the more aromatic quinoxaline analogue 2 did not feature any photocyclization. Further extension of these aromatic systems into helicene-DAE 3 resulted in the stabilization of the cyclized form through the conserved backbone aromaticity, accompanied by enhanced photochromism. This study paves the way toward the generation of aromatic DAE photoswitches for light-controlled molecular systems in the future. |
| Databáze: | OpenAIRE |
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