N-(2-anthryl)-2-[bis(pentafluorophenyl)boryl]benzylideneamine | 1192179-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(2-anthryl)-2-[bis(pentafluorophenyl)boryl]benzylideneamine
• 英文别名: 8-Anthracen-2-yl-7,7-bis(2,3,4,5,6-pentafluorophenyl)-8-azonia-7-boranuidabicyclo[4.3.0]nona-1,3,5,8-tetraene
• CAS: 1192179-02-4
• 化学式: C₃₃H₁₄BF₁₀N
• 分子量: 625.276
• InChiKey: IFZRQUMRWLAWHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  45
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(2-anthryl)-2-[bis(pentafluorophenyl)boryl]benzylideneamine 、 氰化四丁基铵 以 苯 为溶剂， 以96%的产率得到
  参考文献：
  名称：

  Fluorescence Color Change of a Boron-Substituted Diarylazomethine by Reaction with a Cyanide Ion

  摘要：

  在加入等摩尔量的氰离子后，N-(2-蒽基)-2-[双(五氟苯基)硼烷基]苯亚胺的荧光颜色由黄色变为绿色，而 N-苯基衍生物的荧光颜色则发生了淬灭。理论计算表明，N-蒽基亚胺衍生物的荧光颜色变化是通过加合物形成将亚胺基发射转换为蒽基发射实现的。

  DOI：

  10.1246/bcsj.20100145
• 作为产物：
  描述：

  (2-formylphenyl)bis(pentafluorophenyl)borane 、 2-氨基蒽 以 甲苯 为溶剂， 以100%的产率得到N-(2-anthryl)-2-[bis(pentafluorophenyl)boryl]benzylideneamine
  参考文献：
  名称：

  Fluorescence Properties of Simple N-Substituted Aldimines with a B−N Interaction and Their Fluorescence Quenching by a Cyanide Ion

  摘要：

  N-Aryl, A-alkyl, N-alkoxy, and N-amino derivatives of 2-[bis(pentafluorophenyl)boryl]benzylideneamine were synthesized by the condensation reactions of 2-[bis(pentanuorophenyl)boryl]benzaldehyde with the corresponding amines. Their structures were investigated by NMR and Xray crystallographic analysis. Their properties were investigated by UV-vis and fluorescence spectroscopy. The boryl-substituted N-arylimines show blue or green fluorescence in hexane at room temperature, and their fluorescence efficiency is Much higher than that of N-benzylideneaniline. In particular, the boryl-substituted N-(4-dimethylaiminophenyl)imine showed strong green emissions with at least 7000 times higher fluorescence quantum yield (0.73) compared with that of N-benzylideneaniline. The boryl-substituted N-(1-indolyl)- and N-(9-carbazolyl)imines showed dual emissions, one of which was assignable as arising from the lowest singlet excited state and the other from the local excited state of the substituent on the imine nitrogen. The fluorescent properties of the boryl-substituted N-butyl- and N-methoxyimines were also investigated. Reactions of the N-arylimine derivatives with cyanide ion gave the corresponding cyanide adducts and quenched the fluorescence, indicating that these 2-[bis(pentafluorophenyl)boryl]benzylideneamine derivatives have a potential as a cyanide ion sensor.

  DOI：

  10.1021/jo901733b

文献信息

• Fluorescence Properties of Simple N-Substituted Aldimines with a B−N Interaction and Their Fluorescence Quenching by a Cyanide Ion
  作者：Junro Yoshino、Naokazu Kano、Takayuki Kawashima

  DOI：10.1021/jo901733b

  日期：2009.10.2

  N-Aryl, A-alkyl, N-alkoxy, and N-amino derivatives of 2-[bis(pentafluorophenyl)boryl]benzylideneamine were synthesized by the condensation reactions of 2-[bis(pentanuorophenyl)boryl]benzaldehyde with the corresponding amines. Their structures were investigated by NMR and Xray crystallographic analysis. Their properties were investigated by UV-vis and fluorescence spectroscopy. The boryl-substituted N-arylimines show blue or green fluorescence in hexane at room temperature, and their fluorescence efficiency is Much higher than that of N-benzylideneaniline. In particular, the boryl-substituted N-(4-dimethylaiminophenyl)imine showed strong green emissions with at least 7000 times higher fluorescence quantum yield (0.73) compared with that of N-benzylideneaniline. The boryl-substituted N-(1-indolyl)- and N-(9-carbazolyl)imines showed dual emissions, one of which was assignable as arising from the lowest singlet excited state and the other from the local excited state of the substituent on the imine nitrogen. The fluorescent properties of the boryl-substituted N-butyl- and N-methoxyimines were also investigated. Reactions of the N-arylimine derivatives with cyanide ion gave the corresponding cyanide adducts and quenched the fluorescence, indicating that these 2-[bis(pentafluorophenyl)boryl]benzylideneamine derivatives have a potential as a cyanide ion sensor.
• Fluorescence Color Change of a Boron-Substituted Diarylazomethine by Reaction with a Cyanide Ion
  作者：Junro Yoshino、Naokazu Kano、Takayuki Kawashima

  DOI：10.1246/bcsj.20100145

  日期：2010.10.15

  N-(2-Anthryl)-2-[bis(pentafluorophenyl)boryl]benzylideneamine changed its fluorescence color from yellow to green upon addition of an equimolar amount of cyanide ion, in contrast to the N-phenyl derivatives, which showed quenching of the emission. Theoretical calculations suggested that switching of the imine-based emission to anthryl-based emission by adduct formation provides the N-anthrylimine derivative with the fluorescence color change.

  在加入等摩尔量的氰离子后，N-(2-蒽基)-2-[双(五氟苯基)硼烷基]苯亚胺的荧光颜色由黄色变为绿色，而 N-苯基衍生物的荧光颜色则发生了淬灭。理论计算表明，N-蒽基亚胺衍生物的荧光颜色变化是通过加合物形成将亚胺基发射转换为蒽基发射实现的。