The synthesis of novel photochromic diarylethenes bearing a biphenyl moiety and the effects of substitution on their properties |
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| Affiliation: | 1. School of Physics and Astronomy, Beverly and Raymond Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel;2. International Center “Smart Materials”, Southern Federal University, Zorge 5, 344090 Rostov-on-Don, Russia;3. Voronezh State University, Voronezh 394000, Russia;4. CFEL, DESY, Notkestr. 85, 22607 Hamburg, Germany;1. Institut de chimie et procédés pour l’énergie, l’environnement et la santé (ICPEES), LCOSA, UMR CNRS 7515, Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 Rue Becquerel, 67087 Strasbourg Cedex 02, France;2. CEISAM UMR CNRS 6230, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France;3. IUF, 103, Boulevard Saint-Michel, 75005 Paris Cedex 05, France;4. ISCR, CNRS-Université de Rennes 1, 1 Av. du General Leclerc, 35042 Rennes Cedex, France;5. Laboratoire de Cristallochimie, ICSN-CNRS, Bât 27, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France;1. Istituto per lo Studio dei Materiali Nanostrutturati, Consiglio Nazionale delle Ricerche, Dipartimento di Chimica, Sapienza Università di Roma, P .le A. Moro 5, I-00185 Rome, Italy;2. Dipartimento di Chimica, Sapienza Università di Roma, and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, Dipartimento di Chimica, Sapienza Università di Roma, P. le A. Moro 5, I-00185 Rome, Italy;3. Dipartimento S.B.A.I., Sapienza Università di Roma, Via del Castro Laurenziano 7, I-00161 Rome, Italy |
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| Abstract: | A new class of diarylethene bearing a biphenyl moiety was synthesized and the effects of substitution on photochromism, fluorescence and electrochemical character, were investigated. Under alternating irradiation with UV and visible light, the compounds exhibited good photochromism and functioned as fluorescent photoswitches both in solution and in PMMA film. Electron-donating substituents shifted the λmax of the diarylethenes to longer wavelengths and decreased their cyclization quantum yield, while electron-withdrawing substituents greatly increased both cyclization and cycloreversion quantum yield. In addition, cyclic voltammetry revealed that the substituents had a significant effect on the electrochemical behaviour of the diarylethene derivatives. |
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