2-nitro-5a-[2-(4-dimethylaminophenyl)ethylene]-6,6-dimethyl-5a,6-dihydro-12H-indolo-[2,1-b][1,3]benzooxazine | 1140909-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-nitro-5a-[2-(4-dimethylaminophenyl)ethylene]-6,6-dimethyl-5a,6-dihydro-12H-indolo-[2,1-b][1,3]benzooxazine
• CAS: 1140909-94-9
• 化学式: C₂₇H₂₇N₃O₃
• 分子量: 441.53
• InChiKey: YPUXASIYCKNWRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  58.85
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-nitro-5a-[2-(4-dimethylaminophenyl)ethylene]-6,6-dimethyl-5a,6-dihydro-12H-indolo-[2,1-b][1,3]benzooxazine 在 amphiphilic co-polymer 作用下， 生成
  参考文献：
  名称：

  亲水性超分子组装中的快速荧光转换

  摘要：

  我们设计了一种超分子策略，可以在光学控制下调节水中的荧光。它是基于两亲性聚合物疏水内部的荧光团-光敏染料二聚体的截留。二重体周围的聚合物包膜保护它们免受水性环境的侵害，同时在整个超分子构造上施加亲水特性。在所得的组件中，光致变色部件可以在紫外线刺激的影响下在微秒级的时间范围内可逆地操作。反过来，可逆转换控制相邻荧光团的发射强度。结果，这种纳米结构构建体的荧光可以在水中以微秒的切换速度进行数百个循环的光调制。因此，

  DOI：

  10.1002/chem.201201184
• 作为产物：
  描述：

  生成 2-nitro-5a-[2-(4-dimethylaminophenyl)ethylene]-6,6-dimethyl-5a,6-dihydro-12H-indolo-[2,1-b][1,3]benzooxazine
  参考文献：
  名称：

  Photoswitchable Fluorescent Dyads Incorporating BODIPY and [1,3]Oxazine Components

  摘要：

  We designed and synthesized three compounds incorporating a BODIPY fluorophore and an oxazine photochrome within the same molecular skeleton and differing in the nature of the linker bridging the two functional components. The [1,3]oxazine ring of the photochrome opens in less than 6 ns upon laser excitation in two of the three fluorophore-photochrome dyads. This process generates a 3H-indolium cation with a quantum yield of 0.02-0.05. The photogenerated isomer has a lifetime of 1-3 mu s and reverts to the original species with first-order kinetics. Both photochromic systems tolerate hundreds of switching cycles with no sign of degradation. The visible excitation of the dyads is accompanied by the characteristic fluorescence of the BODIPY component. However, the cationic fragment of their photogenerated isomers can accept an electron or energy from the excited fluorophore. As a result, the photoinduced transformation of the photochromic component within each dyad results in the effective quenching of the BODIPY emission. Indeed, the fluorescence of these photoswitchable compounds can be modulated on a microsecond time scale with excellent fatigue resistance under optical control. Thus, our operating principles and choice of functional components can ultimately lead to the development of valuable photoswitchable fluorescent probes for the super-resolution imaging of biological samples.

  DOI：

  10.1021/jp107116d

文献信息

• Fast and Stable Photochromic Oxazines for Fluorescence Switching
  作者：Erhan Deniz、Massimiliano Tomasulo、Janet Cusido、Salvatore Sortino、Françisco M. Raymo

  DOI：10.1021/la201062h

  日期：2011.10.4

  dyad, however, has a slow switching speed and poor fatigue resistance. To improve both parameters, we developed a new family of photochromic switches based on the photoinduced opening and thermal closing of an oxazine ring. These compounds switch back and forth between ring-closed and -open isomers on nanosecond–microsecond timescales and tolerate thousands of switching cycles with no sign of degradation

  衍射对荧光显微镜的空间分辨率施加的严格限制要求确定可行的策略以在光学控制下切换荧光。在这种情况下，光致变色化合物的光诱导和可逆转变是特别有价值的。实际上，可以对这些分子进行改造以响应光学刺激来调节互补荧光团的发射强度。在此一般设计逻辑的基础上，我们组装了一个功能分子构建体，该构建体由硼二吡咯亚甲基荧光团和硝基螺吡喃荧光染料组成，并证明了前者的发射可以通过后者的相互转换进行调节。但是，这种荧光团-光致染料二色化合物的开关速度较慢，且抗疲劳性较差。为了改善这两个参数，我们基于恶嗪环的光致打开和热闭合，开发了一个新的光致变色开关系列。这些化合物在纳秒至微秒的时间尺度上在闭环和开环异构体之间来回切换，并且可以承受数千次切换循环而没有降解迹象。另外，可以利用适当的发色片段在其可切换的恶嗪环上的附着来响应于一对激发光束的照射而使荧光失活或可逆地失活。具体来说，我们组装了三个二联体，每个二联体均基于硼二
• Electrochromic Switching and Microkinetic Behaviour of Oxazine Derivatives and Their Applications
  作者：Shaoyin Zhu、Minjie Li、Sicheng Tang、Yu-Mo Zhang、Bing Yang、Sean Xiao-An Zhang

  DOI：10.1002/ejoc.201301182

  日期：2014.2

  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

  详细的电致变色特性，包括 2-硝基-(P1) 和 2,8-二硝基-5a-[2-(4-二甲基氨基苯基)乙烯]-6,6-二甲基-5a,6-二氢-12H-的微动力转换行为首次使用双波长时间相关光谱监测方法在溶液和氧化铟锡 (ITO) 装置中研究了吲哚[2,1-b][1,3] 苯并恶嗪 (P2)。与常规螺吡喃衍生物相比，这两种恶嗪衍生物对电刺激表现出更好的抗疲劳性和颜色可逆性。基于实验结果和量子化学计算提出了一种新的电致变色机制。由于吲哚片段的氮对位有吸电子基团，
• Bichromophoric dye derived from benzo[1,3]oxazine system
  作者：Yaroslav Prostota、Jerome Berthet、Stephanie Delbaere、Paulo J. Coelho

  DOI：10.1016/j.dyepig.2012.09.017

  日期：2013.2

  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. (C) 2012 Elsevier Ltd. All rights reserved.
• Dynamic Behavior of Molecular Switches in Crystal under Pressure and Its Reflection on Tactile Sensing
  作者：Yi Wang、Xiao Tan、Yu-Mo Zhang、Shaoyin Zhu、Ivan Zhang、Binhong Yu、Kai Wang、Bing Yang、Minjie Li、Bo Zou、Sean Xiao-An Zhang

  DOI：10.1021/ja511499p

  日期：2015.1.21

  Molecular switches have attracted increasing interest in the past decades, due to their broad applications in data storage, optical gating, smart windows, and so on. However, up till now, most of the molecular switches are operated in solutions or polymer blends with the stimuli of light, heat, and electric fields. Herein, we demonstrate the first pressure-controllable molecular switch of a benzo[1,3]oxazine OX-1 in crystal. Distinct from the light-triggered tautomerization between two optical states, applying hydrostatic pressure on the OX-1 crystal results in large-scale and continuous states across the whole visible light range (from similar to 430 to similar to 700 nm), which has not been achieved with other stimuli. Based on detailed and systematic control experiments and theoretical calculation, the preliminary requirements and mechanism of pressure-dependent tautomerization are fully discussed. The contributions of molecular tautomerization to the large-scale optical modulation are also stressed. Finally, the importance of studying pressure-responsive materials on understanding tactile sensing is also discussed and a possible mechanotransduction mode is proposed.