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Electrochromic Switching and Microkinetic Behaviour of Oxazine Derivatives and Their Applications
Author(s) -
Zhu Shaoyin,
Li Minjie,
Tang Sicheng,
Zhang YuMo,
Yang Bing,
Zhang Sean XiaoAn
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301182
Subject(s) - electrochromism , chemistry , spiropyran , ring (chemistry) , photochemistry , indium tin oxide , indole test , combinatorial chemistry , photochromism , organic chemistry , electrode
Detailed electrochromic properties including the microkinetic switching behaviour of 2‐nitro‐ ( P1 ) and 2,8‐dinitro‐5a‐[2‐(4‐dimethylaminophenyl)ethylene]‐6,6‐dimethyl‐5a,6‐dihydro‐12 H ‐indolo[2,1‐ b ][1,3]benzooxazine ( P2 ) were investigated in both solution and indium tin oxide (ITO) devices with a dual‐wavelength time‐dependent spectra monitoring method for the first time. These two oxazine derivatives displayed improved fatigue resistance and colour reversibility towards electrical stimulation compared with conventional spiropyran derivatives. A new electrochromic mechanism was proposed based on the experimental results and on quantum chemical calculations. Owing to an electron‐withdrawing group para to the nitrogen of the indole fragment, P2 demonstrates better electro‐driven reversibility of structural transformation between ring‐open and ring‐closed isomers than P1 .