6-溴-N,N-二丁基萘-2-胺 | 90133-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-溴-N,N-二丁基萘-2-胺
• 英文名称: 6-bromo-2-(di-n-butylamino)naphthalene
• 英文别名: 6-bromo-N,N-dibutyl-2-naphthylamine；6-Bromo-N,N-dibutylnaphthalen-2-amine
• CAS: 90133-98-5
• 化学式: C₁₈H₂₄BrN
• 分子量: 334.299
• InChiKey: HYWTZZAYOKZIKX-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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-二丁基萘-2-胺 在 palladium diacetate 三(邻甲基苯基)磷 作用下， 以 三乙胺 为溶剂， 反应 72.0h， 生成 1-(4-sulfonatobutyl)-4-<β-<2-(di-n-butylamino)-6-naphthyl>vinyl>pyridinium betaine
  参考文献：
  名称：

  Charge-shift probes of membrane potential. Synthesis

  摘要：

  DOI：

  10.1021/jo00188a006
• 作为产物：
  描述：

  6-溴-2-萘酚 在 ammonium hydroxide 、 亚硫酸氢铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-溴-N,N-二丁基萘-2-胺
  参考文献：
  名称：

  Fluorescence of amphiphilic hemicyanine dyes without free double bonds

  摘要：

  Amphiphilic hemicyanine dyes were obtained by coupling unpolar derivatives of aniline and naphthylamine, respectively, to polar derivatives of pyridinium and isoquinolinium, respectively. These dyes have no free double bond that is prone to photoisomerization. They are effective voltage-sensitive probes in biomembranes. The dyes were characterized by their spectra of absorption and by the spectra, the quantum yields, and the lifetimes of fluorescence. (i) An enhanced polarity of solvents shifts the absorption to the blue and the fluorescence to the red. The solvatochromism is described by an enhancement of the Stokes shift at an invariant 00 energy. (ii) An enhanced polarity lowers the quantum yield of fluorescence by orders of magnitude. The effect is described by an enhancement of nonradiative deactivation at an invariant radiative decay. The enhancements of the Stokes shift and of the nonradiative decay are assigned to two types of intramolecular charge-transfer that couple to polar solvents. The first one is induced by electronic excitation. The second one is induced by intramolecular twist in the excited state. The properties of the dyes in amphiphilic assemblies are discussed in terms of their properties in bulk solvents.

  DOI：

  10.1021/j100119a048

文献信息

• HASSNER, A.;BIRNBAUM, D.;LOEW, L. M., J. ORG. CHEM., 1984, 49, N 14, 2546-2551
  作者：HASSNER, A.、BIRNBAUM, D.、LOEW, L. M.

  DOI：——

  日期：——
• Charge-shift probes of membrane potential. Synthesis
  作者：A. Hassner、D. Birnbaum、L. M. Loew

  DOI：10.1021/jo00188a006

  日期：1984.7
• Fluorescence of amphiphilic hemicyanine dyes without free double bonds
  作者：Heinz Ephardt、Peter Fromherz

  DOI：10.1021/j100119a048

  日期：1993.4

  Amphiphilic hemicyanine dyes were obtained by coupling unpolar derivatives of aniline and naphthylamine, respectively, to polar derivatives of pyridinium and isoquinolinium, respectively. These dyes have no free double bond that is prone to photoisomerization. They are effective voltage-sensitive probes in biomembranes. The dyes were characterized by their spectra of absorption and by the spectra, the quantum yields, and the lifetimes of fluorescence. (i) An enhanced polarity of solvents shifts the absorption to the blue and the fluorescence to the red. The solvatochromism is described by an enhancement of the Stokes shift at an invariant 00 energy. (ii) An enhanced polarity lowers the quantum yield of fluorescence by orders of magnitude. The effect is described by an enhancement of nonradiative deactivation at an invariant radiative decay. The enhancements of the Stokes shift and of the nonradiative decay are assigned to two types of intramolecular charge-transfer that couple to polar solvents. The first one is induced by electronic excitation. The second one is induced by intramolecular twist in the excited state. The properties of the dyes in amphiphilic assemblies are discussed in terms of their properties in bulk solvents.