3-(3-ethynyl-phenylethynyl)-9-propyl-9H-carbazole | 865443-55-6

• 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: 3-(3-ethynyl-phenylethynyl)-9-propyl-9H-carbazole
• 英文别名: 3-[2-(3-ethynylphenyl)ethynyl]-9-propylcarbazole
• CAS: 865443-55-6
• 化学式: C₂₅H₁₉N
• 分子量: 333.433
• InChiKey: AZLOHJSFQGBTCE-UHFFFAOYSA-N

物化性质

• 沸点：
  492.6±41.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(3-ethynyl-phenylethynyl)-9-propyl-9H-carbazole 、 6-bromo-2-octyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 二乙胺 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 反应 18.0h， 以82%的产率得到2-octyl-6-[3-(9-propyl-9H-carbazol-3-ylethynyl)-phenylethynyl]-benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Using Meta Conjugation To Enhance Charge Separation versus Charge Recombination in Phenylacetylene Donor−Bridge−Acceptor Complexes

  摘要：

  A pair of donor-bridge-acceptor electron-transfer complexes, with a carbazole donor and a naphthalimide acceptor connected by either a para- or meta-conjugated phenylacetylene bridge, are synthesized and studied using time-resolved and steady-state spectroscopy. These experiments show that the charge separation times, which depend on the coupling of the donor and acceptor through the excited bridge moiety, are similar for the two molecules (Meta and Para). The charge recombination time, however, is a factor of 10 slower for Meta than for Para. These results are related to changes in the electronic coupling of the bridge depending on its electronic state, and show that meta-conjugated bridges provide a possible motif for the design of asymmetric molecular wires.

  DOI：

  10.1021/ja054543q
• 作为产物：
  描述：

  3-(3-bromo-phenylethynyl)-9-propyl-9H-carbazole 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 二异丙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-(3-ethynyl-phenylethynyl)-9-propyl-9H-carbazole
  参考文献：
  名称：

  Using Meta Conjugation To Enhance Charge Separation versus Charge Recombination in Phenylacetylene Donor−Bridge−Acceptor Complexes

  摘要：

  A pair of donor-bridge-acceptor electron-transfer complexes, with a carbazole donor and a naphthalimide acceptor connected by either a para- or meta-conjugated phenylacetylene bridge, are synthesized and studied using time-resolved and steady-state spectroscopy. These experiments show that the charge separation times, which depend on the coupling of the donor and acceptor through the excited bridge moiety, are similar for the two molecules (Meta and Para). The charge recombination time, however, is a factor of 10 slower for Meta than for Para. These results are related to changes in the electronic coupling of the bridge depending on its electronic state, and show that meta-conjugated bridges provide a possible motif for the design of asymmetric molecular wires.

  DOI：

  10.1021/ja054543q