5-(2,4,6-triisopropylphenyl)-2,8-dimethoxy-3,7-bis[p-(N,N-diphenylamino)phenyl]-5H-dibenzo[b,d]borole | 454182-31-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(2,4,6-triisopropylphenyl)-2,8-dimethoxy-3,7-bis[p-(N,N-diphenylamino)phenyl]-5H-dibenzo[b,d]borole
• 英文别名: 5-(2,4,6-triisopropylphenyl)-2,8-dimethoxy-3,7-bis[p-(N,N-diphenylamino)phenyl]-5H-dibenzo[d,b]borole；4-[2,8-dimethoxy-3-[4-(N-phenylanilino)phenyl]-5-[2,4,6-tri(propan-2-yl)phenyl]benzo[b][1]benzoborol-7-yl]-N,N-diphenylaniline
• CAS: 454182-31-1
• 化学式: C₆₅H₆₁BN₂O₂
• 分子量: 913.023
• InChiKey: WUGQXOLZVLLKBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.84
• 重原子数：
  70
• 可旋转键数：
  14
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四丁基氟化铵 、 5-(2,4,6-triisopropylphenyl)-2,8-dimethoxy-3,7-bis[p-(N,N-diphenylamino)phenyl]-5H-dibenzo[b,d]borole 以 四氢呋喃 为溶剂， 生成 5-fluoro-5-(2,4,6-triisopropylphenyl)-2,8-dimethoxy-3,7-bis[p-(N,N-diphenylamino)phenyl]-5H-dibenzo[d,b]borole anion
  参考文献：
  名称：

  Dibenzoborole-Containing π-Electron Systems:  Remarkable Fluorescence Change Based on the “On/Off” Control of the p_π−π* Conjugation

  摘要：

  A series of dibenzoborole derivatives with various groups such as (N,N-diphenylamino)phenyl, thienyl, and bithienyl groups at the 3,7-positions have been synthesized and their photophysical properties studied. These new pi-electron systems show significant solvatochromism in the fluorescence spectra. Thus, about 100-140 nm blue shifts in the emission maxima and 20-30-fold increments in the quantum yields are observed upon changing the solvent from THF to DMF. Similar fluorescence changes are observed upon the addition of n-Bu4NF to their THF solutions, demonstrating their sensing abilities toward a fluoride ion. These fluorescence changes result from the "on/off" control of the ppi-pi* conjugation in their LUMO by the coordination of donor solvents or fluoride ion to the boron atom in the dibenzoborole skeleton.

  DOI：

  10.1021/ja026689k
• 作为产物：
  描述：

  4,4'-dibromo-2,2'-diiodo-5,5'-dimethoxy-1,1'-biphenyl 在 tris(dibenzylideneacetone)dipalladium (0) 、 P(furyl)3 、 叔丁基锂 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 5-(2,4,6-triisopropylphenyl)-2,8-dimethoxy-3,7-bis[p-(N,N-diphenylamino)phenyl]-5H-dibenzo[b,d]borole
  参考文献：
  名称：

  Dibenzoborole-Containing π-Electron Systems:  Remarkable Fluorescence Change Based on the “On/Off” Control of the p_π−π* Conjugation

  摘要：

  A series of dibenzoborole derivatives with various groups such as (N,N-diphenylamino)phenyl, thienyl, and bithienyl groups at the 3,7-positions have been synthesized and their photophysical properties studied. These new pi-electron systems show significant solvatochromism in the fluorescence spectra. Thus, about 100-140 nm blue shifts in the emission maxima and 20-30-fold increments in the quantum yields are observed upon changing the solvent from THF to DMF. Similar fluorescence changes are observed upon the addition of n-Bu4NF to their THF solutions, demonstrating their sensing abilities toward a fluoride ion. These fluorescence changes result from the "on/off" control of the ppi-pi* conjugation in their LUMO by the coordination of donor solvents or fluoride ion to the boron atom in the dibenzoborole skeleton.

  DOI：

  10.1021/ja026689k

文献信息

• A Key Role of Orbital Interaction in the Main Group Element-containing π-Electron Systems
  作者：Shigehiro Yamaguchi、Kohei Tamao

  DOI：10.1246/cl.2005.2

  日期：2005.1

  Various types of main group element-containing π-electron systems have been synthesized using silole, dibenzoborole, or bis-silicon-bridged stilbene as the key building units. In these π-electron systems, the orbital interaction between the main group element moiety and the π-conjugated framework, such as p π -π* and σ*-π* conjugation, plays a crucial role in determining their characteristic electronic

  已经使用silole、dibenzoborole或bis-silicon-bridged stilbene作为关键构建单元合成了各种类型的含主族元素的π-电子系统。在这些 π 电子系统中，主族元素部分与 π 共轭骨架之间的轨道相互作用，如 p π -π* 和 σ*-π* 共轭，在决定它们的特征电子结构方面起着至关重要的作用，并使得它们是用于有机电子和光电子应用的有前途的材料。