3-((9,10-bis(octyloxy)phenanthren-3-yl)ethynyl)-6-ethynyl-9,10-bis(octyloxy)phenanthrene | 1425054-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-((9,10-bis(octyloxy)phenanthren-3-yl)ethynyl)-6-ethynyl-9,10-bis(octyloxy)phenanthrene
• 英文别名: 3-[2-(9,10-Dioctoxyphenanthren-3-yl)ethynyl]-6-ethynyl-9,10-dioctoxyphenanthrene；3-[2-(9,10-dioctoxyphenanthren-3-yl)ethynyl]-6-ethynyl-9,10-dioctoxyphenanthrene
• CAS: 1425054-00-7
• 化学式: C₆₄H₈₂O₄
• 分子量: 915.353
• InChiKey: PJWKEKZSNYGZRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.7
• 重原子数：
  68
• 可旋转键数：
  35
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((9,10-bis(octyloxy)phenanthren-3-yl)ethynyl)-6-ethynyl-9,10-bis(octyloxy)phenanthrene 、 6,6′-(9,10-bis(octyloxy)phenanthrene-3,6-diyl)bis(ethyne-2,1-diyl)bis(3-bromo-9,10-bis(octyloxy)phenanthrene) 在 copper(l) iodide 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 三乙胺 为溶剂， 反应 8.17h， 以52%的产率得到6,6′-(9,10-bis(octyloxy)phenanthrene-3,6-diyl)bis(ethyne-2,1-diyl)bis(3-((6-((9,10-bis(octyloxy)phenanthren-3-yl)-ethynyl)-9,10-bis(octyloxy)phenanthren-3-yl)ethynyl)-9,10-bis(octyloxy)phenanthrene)
  参考文献：
  名称：

  Oligo(3,6-phenanthrene ethynylenes): Synthesis, Characterization, and Photoluminescence

  摘要：

  A series of highly fluorescent, oligo(3,6-phenanthrene ethynylenes) (F1-F7) were synthesized, and their photophysical behavior was systematically investigated. They emitted light with highly emissive quantum yields, up to 0.92. Emissive wavelengths of these compounds relied on the number of phenanthrene blocks existing in the oligomers. Red-shifted emissions were observed as the number of phenanthrenes increased. On the basis of theoretical calculations, helical structures could be formed for F4-F7, indicating that the excimer emissions might be observed for F4-F7 due to the intramolecular pi-pi stackings of phenanthrenes in the helical structures. However, excimer emissions were only observed for F5-F7 in dilute cyclohexane and for F6 and F7 in dilute methylene chloride, respectively. No excimer emission was observed for F4-F7 in dilute tetrahydrofuran due to the degree of solvation.

  DOI：

  10.1021/jo302825r
• 作为产物：
  描述：

  3-溴-9,10-菲醌 在 potassium fluoride 、 sodium persulfate 、 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 三乙胺 为溶剂， 反应 66.59h， 生成 3-((9,10-bis(octyloxy)phenanthren-3-yl)ethynyl)-6-ethynyl-9,10-bis(octyloxy)phenanthrene
  参考文献：
  名称：

  Oligo(3,6-phenanthrene ethynylenes): Synthesis, Characterization, and Photoluminescence

  摘要：

  A series of highly fluorescent, oligo(3,6-phenanthrene ethynylenes) (F1-F7) were synthesized, and their photophysical behavior was systematically investigated. They emitted light with highly emissive quantum yields, up to 0.92. Emissive wavelengths of these compounds relied on the number of phenanthrene blocks existing in the oligomers. Red-shifted emissions were observed as the number of phenanthrenes increased. On the basis of theoretical calculations, helical structures could be formed for F4-F7, indicating that the excimer emissions might be observed for F4-F7 due to the intramolecular pi-pi stackings of phenanthrenes in the helical structures. However, excimer emissions were only observed for F5-F7 in dilute cyclohexane and for F6 and F7 in dilute methylene chloride, respectively. No excimer emission was observed for F4-F7 in dilute tetrahydrofuran due to the degree of solvation.

  DOI：

  10.1021/jo302825r

文献信息

• Oligo(3,6-phenanthrene ethynylenes): Synthesis, Characterization, and Photoluminescence
  作者：Jichao Li、Gongfang Hu、Ningning Wang、Tao Hu、Qiaodong Wen、Ping Lu、Yanguang Wang

  DOI：10.1021/jo302825r

  日期：2013.4.5

  A series of highly fluorescent, oligo(3,6-phenanthrene ethynylenes) (F1-F7) were synthesized, and their photophysical behavior was systematically investigated. They emitted light with highly emissive quantum yields, up to 0.92. Emissive wavelengths of these compounds relied on the number of phenanthrene blocks existing in the oligomers. Red-shifted emissions were observed as the number of phenanthrenes increased. On the basis of theoretical calculations, helical structures could be formed for F4-F7, indicating that the excimer emissions might be observed for F4-F7 due to the intramolecular pi-pi stackings of phenanthrenes in the helical structures. However, excimer emissions were only observed for F5-F7 in dilute cyclohexane and for F6 and F7 in dilute methylene chloride, respectively. No excimer emission was observed for F4-F7 in dilute tetrahydrofuran due to the degree of solvation.