3,6-dibromo-9,10-bis(octyloxy)phenanthrene | 1425053-94-6

• 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: 3,6-dibromo-9,10-bis(octyloxy)phenanthrene
• 英文别名: 3,6-Dibromo-9,10-dioctoxyphenanthrene；3,6-dibromo-9,10-dioctoxyphenanthrene
• CAS: 1425053-94-6
• 化学式: C₃₀H₄₀Br₂O₂
• 分子量: 592.454
• InChiKey: WWQBXNLPCKETMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-dibromo-9,10-bis(octyloxy)phenanthrene 在 potassium fluoride 、 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三苯基膦 作用下， 以 甲醇 、 三乙胺 为溶剂， 反应 18.17h， 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
• 作为产物：
  描述：

  3,6-二溴菲醌 在 sodium dithionite 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 30.0h， 生成 3,6-dibromo-9,10-bis(octyloxy)phenanthrene
  参考文献：
  名称：

  从平面大环到圆柱分子：菲基冠状纳米环作为[6,6]碳纳米管的一部分的合成与性能

  摘要：

  在本文中，我们探索菲作为构成基元，通过Diels-Alder反应从平面大环环合成环状[6,6]碳纳米管片段。基于菲的冠状纳米环7已通过HR-MS，NMR和其他分光光度法进行了全面表征。此外，还研究了其光物理性质以及7和富勒烯C 60之间的超分子相互作用。这项目前的工作提出了一种易于使用的Diels-Alder反应策略来合成圆柱形纳米环。

  DOI：

  10.1021/acs.orglett.9b02055

文献信息

• Study of the controlled chain-growth polymerization of poly(3,6-phenanthrene)
  作者：Michiel Verswyvel、Charly Hoebers、Julien De Winter、Pascal Gerbaux、Guy Koeckelberghs

  DOI：10.1002/pola.26938

  日期：2013.12.1

  ABSTRACTThis manuscript investigates the possibilities to obtain helical conjugated polymers following a controlled chain‐growth polymerization mechanism with external initiation. Attempts to prepare poly(3,6‐(9,10‐di(octyloxy))phenanthrene)s with the existing chain‐growth mechanisms using existing Kumada or Negishi couplings were unsuccessful because of the difficulty to quantitatively prepare the Grignard metathesis reagent starting from the envisaged precursor, namely 3,6‐dibromo‐(9,10‐di(octyloxy))phenanthrene. On the other hand, a Suzuki–Miyaura coupling polymerization using Pd(PtBu3) as the catalyst clearly allows the polymerization to proceed. The reaction conditions were optimized and an in‐depth study with gel permeation chromatography and matrix‐assisted laser desorption ionization time‐of‐flight (MALDI‐ToF) of the underlying mechanisms was performed. Nevertheless, a prolonged chain‐growth mechanism was not achieved for the targeted polymers. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 5067–5074
• 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.
• From Planar Macrocycle to Cylindrical Molecule: Synthesis and Properties of a Phenanthrene-Based Coronal Nanohoop as a Segment of [6,6]Carbon Nanotube
  作者：Shengsheng Cui、Qiang Huang、Jinyi Wang、Hongxing Jia、Pingsen Huang、Shengda Wang、Pingwu Du

  DOI：10.1021/acs.orglett.9b02055

  日期：2019.8.2

  Herein, we explore phenanthrene as the building block to synthesize a hoop-shaped [6,6]carbon nanotube segment from a planar macocycle via a Diels–Alder reaction. The phenanthrene-based coronal nanohoop 7 was fully characterized by HR-MS, NMR, and other spectroscopies. In addition, its photophysical properties and the supramolecular interactions between 7 and fullerene C60 were investigated. This present

  在本文中，我们探索菲作为构成基元，通过Diels-Alder反应从平面大环环合成环状[6,6]碳纳米管片段。基于菲的冠状纳米环7已通过HR-MS，NMR和其他分光光度法进行了全面表征。此外，还研究了其光物理性质以及7和富勒烯C 60之间的超分子相互作用。这项目前的工作提出了一种易于使用的Diels-Alder反应策略来合成圆柱形纳米环。