3,6-diphenyl-4,5-diaza-9,9'-spirobifluorene | 1404084-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3,6-diphenyl-4,5-diaza-9,9'-spirobifluorene
• 英文别名: 4,12-Diphenylspiro[3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene-8,9'-fluorene]；4,12-diphenylspiro[3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene-8,9'-fluorene]
• CAS: 1404084-16-7
• 化学式: C₃₅H₂₂N₂
• 分子量: 470.573
• InChiKey: WGEUQNPBNDBQQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 (1-(2,4-difluorophenyl)-1H-pyrazole)₂Ir(μ-Cl)₂Ir(1-(2,4-difluorophenyl)-1H-pyrazole)₂ 、 3,6-diphenyl-4,5-diaza-9,9'-spirobifluorene 以 乙二醇 为溶剂， 反应 16.0h， 以65%的产率得到[Ir(1-(4,6-difluorophenyl)-pyrazolato-C²,N)₂(3,6-diphenyl-4,5-diaza-9,9'-spirobifluorene)](PF₆)
  参考文献：
  名称：

  Cationic Iridium Complexes with Intramolecular π–π Interaction and Enhanced Steric Hindrance for Solid-State Light-Emitting Electrochemical Cells

  摘要：

  Cationic iridium complexes incorporated 4,5-diaza-9,9'-spirobifluorene as N<^>N ancillary ligands, in which one (2) or two (3) phenyl groups were introduced onto 4,5-diazafluorene to afford intraligand pi-pi interactions. The X-ray crystal structures of complexes 2 and 3 show that the pendant phenyl ring forms strong intramolecular face-to-face pi-stacking with the difluorophenyl ring of the cyclometalated ligand with distances of 3.38 angstrom for complex 2 and 3.40 and 3.46 angstrom for complex 3. This pi-pi stacking interaction minimizes the expansion of the metal ligand bonds in the excited state, resulting in a longer device lifetime in the light-emitting electrochemical cell (LEC) devices.

  DOI：

  10.1021/ic300673k
• 作为产物：
  描述：

  3-phenyl-4,5-diaza-9,9'-spirobifluorene 、 苯基锂 在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 反应 9.0h， 生成 3,6-diphenyl-4,5-diaza-9,9'-spirobifluorene
  参考文献：
  名称：

  Cationic Iridium Complexes with Intramolecular π–π Interaction and Enhanced Steric Hindrance for Solid-State Light-Emitting Electrochemical Cells

  摘要：

  Cationic iridium complexes incorporated 4,5-diaza-9,9'-spirobifluorene as N<^>N ancillary ligands, in which one (2) or two (3) phenyl groups were introduced onto 4,5-diazafluorene to afford intraligand pi-pi interactions. The X-ray crystal structures of complexes 2 and 3 show that the pendant phenyl ring forms strong intramolecular face-to-face pi-stacking with the difluorophenyl ring of the cyclometalated ligand with distances of 3.38 angstrom for complex 2 and 3.40 and 3.46 angstrom for complex 3. This pi-pi stacking interaction minimizes the expansion of the metal ligand bonds in the excited state, resulting in a longer device lifetime in the light-emitting electrochemical cell (LEC) devices.

  DOI：

  10.1021/ic300673k

文献信息

• Cationic Iridium Complexes with Intramolecular π–π Interaction and Enhanced Steric Hindrance for Solid-State Light-Emitting Electrochemical Cells
  作者：Hsiao-Fan Chen、Wen-Yi Hung、Shou-Wei Chen、Ting-Chih Wang、Shih-Wei Lin、Shu-Hua Chou、Chih-Teng Liao、Hai-Ching Su、Hsiao-An Pan、Pi-Tai Chou、Yi-Hung Liu、Ken-Tsung Wong

  DOI：10.1021/ic300673k

  日期：2012.11.19

  Cationic iridium complexes incorporated 4,5-diaza-9,9'-spirobifluorene as N<^>N ancillary ligands, in which one (2) or two (3) phenyl groups were introduced onto 4,5-diazafluorene to afford intraligand pi-pi interactions. The X-ray crystal structures of complexes 2 and 3 show that the pendant phenyl ring forms strong intramolecular face-to-face pi-stacking with the difluorophenyl ring of the cyclometalated ligand with distances of 3.38 angstrom for complex 2 and 3.40 and 3.46 angstrom for complex 3. This pi-pi stacking interaction minimizes the expansion of the metal ligand bonds in the excited state, resulting in a longer device lifetime in the light-emitting electrochemical cell (LEC) devices.