2,9-bis(4-octyloxyphenyl)-1,10-phenanthroline-5,6-dione | 1245902-40-2

• 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: 2,9-bis(4-octyloxyphenyl)-1,10-phenanthroline-5,6-dione
• 英文别名: 2,9-Bis(4-octoxyphenyl)-1,10-phenanthroline-5,6-dione
• CAS: 1245902-40-2
• 化学式: C₄₀H₄₆N₂O₄
• 分子量: 618.816
• InChiKey: OVQLUYDRFBYLAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,9-bis(4-octyloxyphenyl)-1,10-phenanthroline-5,6-dione 、 hexaaminobenzene trihydrochloride 在 溶剂黄146 、 sodium carbonate 作用下， 以 氯仿 、 水 为溶剂， 反应 12.5h， 以41%的产率得到3,6,13,16,23,26-hexakis(4-octyloxyphenyl)tri-1,10-phenanthrolino[5,6-b:5',6'-h:5'',6''-n]-1,4,5,8,9,12-hexaazatriphenylene
  参考文献：
  名称：

  Expanded π-Electron Systems, Tri(phenanthro)hexaazatriphenylenes and Tri(phenanthrolino)hexaazatriphenylenes, That Are Self-Assembled To Form One-Dimensional Aggregates

  摘要：

  This paper reports the self-assembling and electrochemical nature of hexaazatriphenylene-based electron-deficient heteroaromatics with an expanded pi-electron system The tri(phenanthro)hexaazatriphenylenes (TPHAT-Cs) and tri(phenanthrolino)hexaazatriphenylenes (TPHAT-Ns) were prepared by condensation reactions or the corresponding phenanthrenequinonones and phenanthrolinediones respectively. with hexaaminobenzene Their election affinity was indicated from cyclic voltammetry measurements. In which the first reduction potentials were evaluated at mound -1 7 V (vs Fc/Fe+) in dichloromethane In nonpolar and polar solvents and in the film state. the TPHAT-Cs and TPHAT-Ns formed one-dimensional aggregates with an H-type stacking mode. In the MALDI-TOF mass spectra significant peaks were seen at several multiples of the parent ion up to tell;liner aggregates The NMR spectra indicated a line-broadening effect due to the aggregation The UV-vis and fluorescence spectra showed a concentration dependence which is. attributed to a dynamic exchange between the monomer and aggregate species The older of the aggregative nature was estimated from the concentration dependence and the fluorescence quantum yield By replacement of the peripheral aromatic moieties instead of the phenanthiene (TPHAT-Cs) with the phenanthroline (TPHAT-Ns). the aggregative nature was enhanced

  DOI：

  10.1021/jo101212d
• 作为产物：
  描述：

  2,9-二溴-1,10-菲咯啉-5,6-二酮 、 2,2-dimethyl-1,3-propanediyl 4-octyloxyphenylboronate 在 四(三苯基膦)钯 、 水 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.08h， 以52%的产率得到2,9-bis(4-octyloxyphenyl)-1,10-phenanthroline-5,6-dione
  参考文献：
  名称：

  Expanded π-Electron Systems, Tri(phenanthro)hexaazatriphenylenes and Tri(phenanthrolino)hexaazatriphenylenes, That Are Self-Assembled To Form One-Dimensional Aggregates

  摘要：

  This paper reports the self-assembling and electrochemical nature of hexaazatriphenylene-based electron-deficient heteroaromatics with an expanded pi-electron system The tri(phenanthro)hexaazatriphenylenes (TPHAT-Cs) and tri(phenanthrolino)hexaazatriphenylenes (TPHAT-Ns) were prepared by condensation reactions or the corresponding phenanthrenequinonones and phenanthrolinediones respectively. with hexaaminobenzene Their election affinity was indicated from cyclic voltammetry measurements. In which the first reduction potentials were evaluated at mound -1 7 V (vs Fc/Fe+) in dichloromethane In nonpolar and polar solvents and in the film state. the TPHAT-Cs and TPHAT-Ns formed one-dimensional aggregates with an H-type stacking mode. In the MALDI-TOF mass spectra significant peaks were seen at several multiples of the parent ion up to tell;liner aggregates The NMR spectra indicated a line-broadening effect due to the aggregation The UV-vis and fluorescence spectra showed a concentration dependence which is. attributed to a dynamic exchange between the monomer and aggregate species The older of the aggregative nature was estimated from the concentration dependence and the fluorescence quantum yield By replacement of the peripheral aromatic moieties instead of the phenanthiene (TPHAT-Cs) with the phenanthroline (TPHAT-Ns). the aggregative nature was enhanced

  DOI：

  10.1021/jo101212d