| 1233087-77-8

• CAS: 1233087-77-8
• 化学式: C₅₁H₅₂BF₂N₅O₅
• 分子量: 863.812
• InChiKey: SXZJMNFXQGSFQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  在 三氟乙酸 作用下， 生成 (3S,4R)-3-methylundec-1-en-4-ol
  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
• 作为产物：
  描述：

  2,3,3-三甲基-5-甲氧基-3H-吲哚 在 4-二甲氨基吡啶 、 氢溴酸 、 三溴化硼 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 124.0h， 生成
  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