6-溴-N,N-二己基蒽-2-胺 | 919992-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 6-溴-N,N-二己基蒽-2-胺
• 英文名称: 2-bromo-6-dihexylaminoanthracene
• 英文别名: 6-Bromo-N,N-dihexylanthracen-2-amine
• CAS: 919992-04-4
• 化学式: C₂₆H₃₄BrN
• 分子量: 440.467
• InChiKey: LHMYCNFMHIWUTP-UHFFFAOYSA-N

物化性质

• 沸点：
  555.0±25.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-溴-N,N-二己基蒽-2-胺 在 copper(l) chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 6-propionyl-2-(dihexylamino)anthracene
  参考文献：
  名称：

  Long-Wavelength Analogue of PRODAN:  Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

  摘要：

  We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polarity-sensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.

  DOI：

  10.1021/jo0616660
• 作为产物：
  描述：

  2-溴-6-(二己基氨基)蒽-9,10-二酮 在 sodium tetrahydroborate 、 盐酸 作用下， 以 异丙醇 为溶剂， 反应 26.0h， 以53%的产率得到6-溴-N,N-二己基蒽-2-胺
  参考文献：
  名称：

  Long-Wavelength Analogue of PRODAN:  Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

  摘要：

  We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polarity-sensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.

  DOI：

  10.1021/jo0616660

文献信息

• Long-Wavelength Analogue of PRODAN:  Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure
  作者：Zhikuan Lu、Samuel J. Lord、Hui Wang、W. E. Moerner、Robert J. Twieg

  DOI：10.1021/jo0616660

  日期：2006.12.1

  We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polarity-sensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.