E/Z-5-(7-N,N-dibutylamino-1-phenanthryl)vinylisoquinoline | 591253-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: E/Z-5-(7-N,N-dibutylamino-1-phenanthryl)vinylisoquinoline
• 英文别名: N,N-Dibutyl-8-[2-(isoquinolin-5-YL)ethenyl]phenanthren-2-amine；N,N-dibutyl-8-(2-isoquinolin-5-ylethenyl)phenanthren-2-amine
• CAS: 591253-61-1
• 化学式: C₃₃H₃₄N₂
• 分子量: 458.646
• InChiKey: PPAAWAQSOGKOGN-UHFFFAOYSA-N

物化性质

• 沸点：
  670.4±24.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  E/Z-5-(7-N,N-dibutylamino-1-phenanthryl)vinylisoquinoline 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 11-N,N-dibutylaminobenzo[m]-3-azapicene
  参考文献：
  名称：

  Anellated Hemicyanine Dyes with Large Symmetrical Solvatochromism of Absorption and Fluorescence

  摘要：

  A novel class of amphiphilic hemicyanine dyes is described where electron-pushing aniline and electron-pulling pyridinium are joined by anellated benzene rings. Enhancing the solvent polarity, the absorption band of these ANNINE dyes is shifted to the blue and the fluorescence band is shifted to the red at an invariant 00 energy. The increasing Stokes shift spans the whole visible spectrum. The divergent symmetrical solvatochromism of the positively charged chromophores is parametrized by a monopole-dipole model using a Born-Onsager-Marcus approach. From the intramolecular charge shift that is induced by electronic excitation, the linear Stark effect that is expected when the ANNINE dyes are used as voltage-sensitive probes in a biomembrane is estimated.

  DOI：

  10.1021/jp0345809
• 作为产物：
  描述：

  7-N,N-dibutylamino-1-bromomethylphenanthrene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 E/Z-5-(7-N,N-dibutylamino-1-phenanthryl)vinylisoquinoline
  参考文献：
  名称：

  Anellated Hemicyanine Dyes with Large Symmetrical Solvatochromism of Absorption and Fluorescence

  摘要：

  A novel class of amphiphilic hemicyanine dyes is described where electron-pushing aniline and electron-pulling pyridinium are joined by anellated benzene rings. Enhancing the solvent polarity, the absorption band of these ANNINE dyes is shifted to the blue and the fluorescence band is shifted to the red at an invariant 00 energy. The increasing Stokes shift spans the whole visible spectrum. The divergent symmetrical solvatochromism of the positively charged chromophores is parametrized by a monopole-dipole model using a Born-Onsager-Marcus approach. From the intramolecular charge shift that is induced by electronic excitation, the linear Stark effect that is expected when the ANNINE dyes are used as voltage-sensitive probes in a biomembrane is estimated.

  DOI：

  10.1021/jp0345809

文献信息

• Anellated Hemicyanine Dyes with Large Symmetrical Solvatochromism of Absorption and Fluorescence
  作者：Gerd Hübener、Armin Lambacher、Peter Fromherz

  DOI：10.1021/jp0345809

  日期：2003.8.1

  A novel class of amphiphilic hemicyanine dyes is described where electron-pushing aniline and electron-pulling pyridinium are joined by anellated benzene rings. Enhancing the solvent polarity, the absorption band of these ANNINE dyes is shifted to the blue and the fluorescence band is shifted to the red at an invariant 00 energy. The increasing Stokes shift spans the whole visible spectrum. The divergent symmetrical solvatochromism of the positively charged chromophores is parametrized by a monopole-dipole model using a Born-Onsager-Marcus approach. From the intramolecular charge shift that is induced by electronic excitation, the linear Stark effect that is expected when the ANNINE dyes are used as voltage-sensitive probes in a biomembrane is estimated.