1140909-94-9Relevant academic research and scientific papers
Electrochromic switching and microkinetic behaviour of oxazine derivatives and their applications
Zhu, Shaoyin,Li, Minjie,Tang, Sicheng,Zhang, Yu-Mo,Yang, Bing,Zhang, Sean Xiao-An
, p. 1227 - 1235 (2014/03/21)
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-12H-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. The electrochromic behaviour of oxazine derivatives indicates that oxidation of the central nitrogen moiety switches the derivatives with concomitant colour change. The reversibility, chemical stability, and fatigue resistance towards electric stimulation depends on the substituents present, with an electron-withdrawing group para to the nitrogen of the indole fragment being beneficial. Copyright
Electrochromic Switching and Microkinetic Behaviour of Oxazine Derivatives and Their Applications
Zhu, Shaoyin,Li, Minjie,Tang, Sicheng,Zhang, Yu-Mo,Yang, Bing,Zhang, Sean Xiao-An
, p. 1227 - 1235 (2015/10/05)
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-12H-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. The electrochromic behaviour of oxazine derivatives indicates that oxidation of the central nitrogen moiety switches the derivatives with concomitant colour change. The reversibility, chemical stability, and fatigue resistance towards electric stimulation depends on the substituents present, with an electron-withdrawing group para to the nitrogen of the indole fragment being beneficial.
Bichromophoric dye derived from benzo[1,3]oxazine system
Prostota, Yaroslav,Berthet, Jerome,Delbaere, Stephanie,Coelho, Paulo J.
, p. 569 - 573 (2013/02/23)
The reaction of 2-methylbenzo[1,3]oxazine with julolidine-9-carbaldehyde under acid catalysis afforded an highly coloured blue dye with an intense absorption at 591 nm. NMR and UV-Vis analysis showed that this compound has an opened oxazine structure with a polymethine-type chromophore, corresponding to a protonated thermally stable coloured form of photochromic benzo[1,3]oxazines that are known to be unstable at room temperature with lifetimes in the ns timescale. In basic medium this dye is converted into a stable opened zwitterionic form of photochromic benzo[1,3]oxazines with two absorption maxima at 410 and 587 nm assigned to conjugated 3H-indolium and 4-nitrophenolate chromophores respectively.
