1-ethynyl-2,5-bis(dimesitylboryl)-4-[4-(N,N-diphenylamino)phenylethynyl]benzene | 919364-31-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-ethynyl-2,5-bis(dimesitylboryl)-4-[4-(N,N-diphenylamino)phenylethynyl]benzene
• CAS: 919364-31-1
• 化学式: C₆₄H₆₁B₂N
• 分子量: 865.817
• InChiKey: UKBGKOBFMPMJQV-UHFFFAOYSA-N

物化性质

• 沸点：
  893.5±65.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.27
• 重原子数：
  67.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-ethynyl-2,5-bis(dimesitylboryl)-4-[4-(N,N-diphenylamino)phenylethynyl]benzene 、 1,4-二碘苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以76%的产率得到1,4-bis{2,5-bis(dimesitylboryl)-4-[4-(N,N-diphenylamino)phenylethynyl]phenylethynyl}benzene
  参考文献：
  名称：

  Highly Emissive Organic Solids Containing 2,5-Diboryl-1,4-phenylene Unit

  摘要：

  We disclosed a series of pi-conjugated systems containing 2,5-bis(dimesitylboryl)-1,4-phenylene as the core unit and electron-donating amino groups at the terminal positions. The extension of the ppi-pi* conjugation in the diborylphenylene moiety along the short axis of the pi-conjugated framework as well as the incorporation of two bulky dimesitylboryl groups at the para-positions makes this moiety act as a unique bulky pi-electron-accepting unit. As a consequence, these systems behave like donor-acceptor-donor quadrupolar pi-electron systems and show a large solvatochromism in the fluorescence spectra. Moreover, these organoboron pi systems exhibit intense fluorescence even in the solid state with the quantum yields of 0.73-0.90.

  DOI：

  10.1021/ja0637550
• 作为产物：
  描述：

  [2-[2,5-二溴-4-[2-(三甲基硅基)乙炔基]苯基]乙炔基]三甲基硅烷 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 108.5h， 生成 1-ethynyl-2,5-bis(dimesitylboryl)-4-[4-(N,N-diphenylamino)phenylethynyl]benzene
  参考文献：
  名称：

  Highly Emissive Organic Solids Containing 2,5-Diboryl-1,4-phenylene Unit

  摘要：

  We disclosed a series of pi-conjugated systems containing 2,5-bis(dimesitylboryl)-1,4-phenylene as the core unit and electron-donating amino groups at the terminal positions. The extension of the ppi-pi* conjugation in the diborylphenylene moiety along the short axis of the pi-conjugated framework as well as the incorporation of two bulky dimesitylboryl groups at the para-positions makes this moiety act as a unique bulky pi-electron-accepting unit. As a consequence, these systems behave like donor-acceptor-donor quadrupolar pi-electron systems and show a large solvatochromism in the fluorescence spectra. Moreover, these organoboron pi systems exhibit intense fluorescence even in the solid state with the quantum yields of 0.73-0.90.

  DOI：

  10.1021/ja0637550