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Molecular design for a write-by-light/erase-by-heat recording system using photochromic diarylethenes with thermal cycloreversion
Institution:1. Department of Physics, Dalian Maritime University, Dalian 110623, People''s Republic of China;2. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, People''s Republic of China;3. Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People''s Republic of China;4. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People''s Republic of China;1. Faculty of Chemistry, Opole University, Oleska 48, 45-052, Opole, Poland;2. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland;3. Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland;1. School of Electrical and Information Engineering, Heilongjiang University of Science and Technology, Harbin 150022, China;2. School of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, China;1. Key Laboratory of Small Functional Organic Molecule, Ministry of Education and Jiangxi''s Key Laboratory of Green Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, PR China;2. Department of Obstetrics and Gynecology, Jiangxi Provincial People''s Hospital, Nanchang, Jiangxi 330006, PR China
Abstract:We designed and synthesized photochromic diarylethenes for a write-by-light/erase-by-heat recording system. The introduction of polar substituents at both sides of the diarylethene maintained the photocyclization and photocycloreversion reactivities, but significantly affected the thermal cycloreversion reactivity. The introduction of electron-withdrawing substituents accelerated the thermal reaction and the introduction of electron-donating substituents suppressed the thermal reaction. The rate constants of the thermal reaction were well correlated with Brown-Okamoto's substituent constant σ+ that is a modified value of Hammett's substituent constant σ. The large rate constants are ascribed to the lower activation energy for the thermal reaction. These results provide new knowledge for the molecular design of diarylethenes for a write-by-light/erase-by-heat recording system.
Keywords:Photochromism  Diarylethene  Substituent effect  Thermal reactivity  Substituent constant
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