8-Carbazol-9-yl-7,7-bis(2,3,4,5,6-pentafluorophenyl)-8-azonia-7-boranuidabicyclo[4.3.0]nona-1,3,5,8-tetraene | 1192179-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 8-Carbazol-9-yl-7,7-bis(2,3,4,5,6-pentafluorophenyl)-8-azonia-7-boranuidabicyclo[4.3.0]nona-1,3,5,8-tetraene
• CAS: 1192179-05-7
• 化学式: C₃₁H₁₃BF₁₀N₂
• 分子量: 614.253
• InChiKey: SHEUTNVHDKYDAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  44
• 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：
  7.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  N-氨基咔唑 、 (2-formylphenyl)bis(pentafluorophenyl)borane 以 甲苯 为溶剂， 以100%的产率得到8-Carbazol-9-yl-7,7-bis(2,3,4,5,6-pentafluorophenyl)-8-azonia-7-boranuidabicyclo[4.3.0]nona-1,3,5,8-tetraene
  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.