Benzothiophene or Benzofuran Bridges in Diaryl Ethenes: Two‐Step Access by Pd‐Catalyzed CH Activation and Theoretical/Experimental Studies on Their Photoreactivity |
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| Authors: | Kedong Yuan Dr Julien Boixel Dr Agisilaos Chantzis Prof Denis Jacquemin Dr Véronique Guerchais Dr Henri Doucet |
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| Institution: | 1. Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS‐Université de Rennes 1, “Organométalliques, Matériaux et Catalyse”, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33)?0223236939;2. CEISAM, UMR CNRS 6230, BP 92208, Université de Nantes, 2, Rue de la Houssinière, 44322 Nantes, Cedex 3 (France);3. Institut Universitaire de France (IUF), 105 Blvd St‐Michel, 75005 Paris, Cedex 5 (France) |
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| Abstract: | A series of terarylenes incorporating benzothiophene ( BT )/benzofuran ( BF ) as the central ethene unit was synthesised by using sequential Pd‐catalysed C?H activation reactions. This new methodology allows the easy modification of the nature of the pendant heteroarene groups. Diaryl ethene (DAE) derivatives with thiophene, thiazole, pyrrole, isoxazole and pyrazole rings were prepared. A large number of asymmetrical DAEs are easily accessible by this new method in both the BT and BF series. The study of their photochromic properties in solution revealed that the nature of the heteroarene and of the central unit drastically modify their photochromic behaviour. TD‐DFT calculations were performed to assess the nature of the relevant excited states. |
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| Keywords: | C H activation heterocycles homogeneous catalysis palladium photochromism |
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