9-butyl-3-ethynyl-6-phenylethynylcarbazole | 1310797-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-butyl-3-ethynyl-6-phenylethynylcarbazole
• CAS: 1310797-95-5
• 化学式: C₂₆H₂₁N
• 分子量: 347.459
• InChiKey: FAWDDDAOENUKSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(4-溴苯基)吡啶 、 9-butyl-3-ethynyl-6-phenylethynylcarbazole 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以40%的产率得到
  参考文献：
  名称：

  Tuning the emission property of carbazole-caped cyclometalated platinum(II) complexes and its application for enhanced luminescent oxygen sensing

  摘要：

  Carbazole-caped cyclometalated platinum(II) complexes aryl-R-ppyPt(acac) (where ppy - 4-phenylpyridine, acac acetylacetonato, aryl carbazole and R is linker) were synthesized. The carbazole group is attached to the ppy ligand via alpha-diketo moiety (Pt-1) and (Pt-2) or C-C single bond (Pt-3), by Sonogashira or Negishi coupling reactions. We found that the ethynylene bonds of the C boolean AND N ligands were oxidized to alpha-diketo or methylene-keto structure during the metalation with K2PtCl4. Emissions beyond 550 nm were observed for Pt-1, with electron-withdrawing alpha-diketo moiety attached to ppy ligand, compared to the emission at 486 nm for the parent complex ppyPt(acac). Extended phosphorescence lifetime (tau(P) = 12.4 mu s) and enhanced phosphorescence quantum yield (Phi(P) = 66%) were observed for Pt-3 compared to ppyPt(acac) (tau(P) = 2.4 mu s and Phi P = 15%), we attribute the enhanced phosphorescence property to the electron-donating carbazole substituent. With density functional theoretical calculations (DFT), we found that the carbazole moiety is involved in the HOMO (Pt-3), the alpha-diketo moiety is involved in the LUMO (Pt-1), thus the energy gaps between the HOMO and LUMO in both cases were decreased and red-shifted emission is expected, compared to ppyPt(acac). The different emission properties of 1,2-dione containing complexes (Pt-1 and Pt-2) and the Pt-3 were rationalized by the spin density surface analysis of the complexes. The luminescent O-2 sensing properties of these complexes were studied in solution and in polymer films, for which fast response time (3.3 s) and recovery time (3.7 s) were observed. Two-site model fitting indicated that complex Pt-3 is the most sensitive O-2 sensing material among the complexes studied herein, with quenching constant of K-SV = 0.0238 Torr(-1). (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.03.002
• 作为产物：
  描述：

  3-bromo-9-butyl-6-iodocarbazole 在 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 9-butyl-3-ethynyl-6-phenylethynylcarbazole
  参考文献：
  名称：

  Tuning the emission property of carbazole-caped cyclometalated platinum(II) complexes and its application for enhanced luminescent oxygen sensing

  摘要：

  Carbazole-caped cyclometalated platinum(II) complexes aryl-R-ppyPt(acac) (where ppy - 4-phenylpyridine, acac acetylacetonato, aryl carbazole and R is linker) were synthesized. The carbazole group is attached to the ppy ligand via alpha-diketo moiety (Pt-1) and (Pt-2) or C-C single bond (Pt-3), by Sonogashira or Negishi coupling reactions. We found that the ethynylene bonds of the C boolean AND N ligands were oxidized to alpha-diketo or methylene-keto structure during the metalation with K2PtCl4. Emissions beyond 550 nm were observed for Pt-1, with electron-withdrawing alpha-diketo moiety attached to ppy ligand, compared to the emission at 486 nm for the parent complex ppyPt(acac). Extended phosphorescence lifetime (tau(P) = 12.4 mu s) and enhanced phosphorescence quantum yield (Phi(P) = 66%) were observed for Pt-3 compared to ppyPt(acac) (tau(P) = 2.4 mu s and Phi P = 15%), we attribute the enhanced phosphorescence property to the electron-donating carbazole substituent. With density functional theoretical calculations (DFT), we found that the carbazole moiety is involved in the HOMO (Pt-3), the alpha-diketo moiety is involved in the LUMO (Pt-1), thus the energy gaps between the HOMO and LUMO in both cases were decreased and red-shifted emission is expected, compared to ppyPt(acac). The different emission properties of 1,2-dione containing complexes (Pt-1 and Pt-2) and the Pt-3 were rationalized by the spin density surface analysis of the complexes. The luminescent O-2 sensing properties of these complexes were studied in solution and in polymer films, for which fast response time (3.3 s) and recovery time (3.7 s) were observed. Two-site model fitting indicated that complex Pt-3 is the most sensitive O-2 sensing material among the complexes studied herein, with quenching constant of K-SV = 0.0238 Torr(-1). (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.03.002