5-chloro-3-phenylamino-8-(4-tolyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 877616-05-2

• 英文名称: 5-chloro-3-phenylamino-8-(4-tolyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 3-(aniline-1H)-5-chloro-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)；3-(aniline-1H)-5-chloro-BODIPY
• CAS: 877616-05-2
• 化学式: C₂₂H₁₇BClF₂N₃
• 分子量: 407.658
• InChiKey: RGXCLGQPWYCXCQ-UHFFFAOYSA-N

计算性质

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

• 作为产物：
  描述：

  3,5-dichloro-8-(4-tolyl) BODIPY 、 苯胺 以 乙腈 为溶剂， 以69%的产率得到5-chloro-3-phenylamino-8-(4-tolyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution

  摘要：

  BODIPY色基可以通过对3,5-二氯BODIPY进行O-、N-、S-和C-亲核试剂的单取代或双取代进行简单修改。新BODIPY衍生物的吸收和荧光光谱数据也被报道。

  DOI：

  10.1039/b512756d

文献信息

• BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine
  作者：Li-Ya Niu、Ying-Shi Guan、Yu-Zhe Chen、Li-Zhu Wu、Chen-Ho Tung、Qing-Zheng Yang

  DOI：10.1021/ja309079f

  日期：2012.11.21

  We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.
• Synthesis, Spectroscopy, Crystal Structure, Electrochemistry, and Quantum Chemical and Molecular Dynamics Calculations of a 3-Anilino Difluoroboron Dipyrromethene Dye
  作者：Wenwu Qin、Volker Leen、Taoufik Rohand、Wim Dehaen、Peter Dedecker、Mark Van der Auweraer、Koen Robeyns、Luc Van Meervelt、David Beljonne、Bernard Van Averbeke、John N. Clifford、Kris Driesen、Koen Binnemans、Noël Boens

  DOI：10.1021/jp8077584

  日期：2009.1.15

  An asymmetrically substituted fluorescent difluoroboron dipyrromethene (BODIPY) dye, with a phenylamino group at the 3-position of the BODIPY chromophore, has been synthesized by nucleophilic substitution of 3,5-dichloro-8-(4-tolyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. The solvent-dependent spectroscopic and photophysical properties have been investigated by means of UV-vis spectrophotometry and steady-state and time-resolved fluorometry and reflect the large effect of the anilino substituent on the fluorescence characteristics. The compound has a low fluorescence quantum yield in all but the apolar solvents cyclohexane, toluene, and chloroform. Its emission maxima in a series of solvents from cyclohexane to methanol are red-shifted by approximately 50 nm in comparison to classic BODIPY derivatives. Its oxidation potential in dichloromethane is at ca. 1.14 V versus Ag/AgCl. The absorption bandwidths and Stokes shifts are much larger than those of typical, symmetric difluoroboron dipyrromethene dyes. The values of the fluorescence rate constant are in the (1.4-1.7) x 10(8) s(-1) range and do not vary much between the solvents studied. X-ray diffraction analysis shows that the BODIPY core is planar. Molecular dynamics simulations show that there is no clear indication for aggregates in solution.