2,3-dibromo-6,7,10,11-tetrakis(hexyloxy)triphenylene | 214050-35-8

• 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: 2,3-dibromo-6,7,10,11-tetrakis(hexyloxy)triphenylene
• 英文别名: 2,3-dibromo-6,7,10,11-tetrahexoxytriphenylene
• CAS: 214050-35-8
• 化学式: C₄₂H₅₈Br₂O₄
• 分子量: 786.728
• InChiKey: YPFIJNORDSUGKW-UHFFFAOYSA-N

物化性质

• 沸点：
  777.5±55.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.51
• 重原子数：
  48.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  氰化锌 、 2,3-dibromo-6,7,10,11-tetrakis(hexyloxy)triphenylene 在 tris(dibenzylideneacetone)dipalladium (0) 1,1'-双(二苯基膦)二茂铁 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以28%的产率得到6,7,10,11-Tetrakis-hexyloxy-triphenylene-2,3-dicarbonitrile
  参考文献：
  名称：

  Macrodiscotic triphenylenophthalocyanines

  摘要：

  首次合成了具有高度取代基的三蝶烯酞菁，并发现它们具有介晶性。

  DOI：

  10.1039/b200978a
• 作为产物：
  描述：

  4-溴黎芦醚 在 氢溴酸 、 溴 、 三氯化铁 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 palladium dichloride 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 100.0h， 生成 2,3-dibromo-6,7,10,11-tetrakis(hexyloxy)triphenylene
  参考文献：
  名称：

  摘要：

  A series of novel triphenylenes has been synthesised by a combination of palladium catalysed coupling, oxidative cyclisation, bromination and nucleophilic aromatic substitution. The new derivatives are designed to have structures which are intermediate between the known symmetrical materials hexakis( hexyloxy) triphenylene and hexakis( hexylthio) triphenylene. The compounds having four hexyloxy and two hexylthio substituents form only Col(h) mesophases. Triphenylenes having four hexylthio and two hexyloxy substituents also give Col(h) mesophases but 3,6- bis(hexyloxy)-2,7,10,11-tetrakis(hexylthio) triphenylene 5 is unique in that it cools into a stable, more ordered phase. The low temperature phase, which appears to be indefinitely stable at ambient temperature, is assumed to be helical based on transition enthalpy data.

  DOI：

  10.1039/b103450m

文献信息

• Probing the structural factors influencing columnar mesophase formation and stability in triphenylene discotics
  作者：Andrew N. Cammidge、Céline Chausson、Hemant Gopee、Juanjuan Li、David L. Hughes

  DOI：10.1039/b913678a

  日期：——

  Series of structurally related substituted triphenylene derivatives were designed and synthesised to interrogate key features which determine mesophase formation and stability, and to challenge the general conclusions previously proposed by us and others. It is apparent that no single, simple principle can be universally applied.

  设计并合成了一系列结构相关的替代三苯基衍生物，以探讨决定介相形成和稳定性的关键特征，并挑战我们和其他人之前提出的一般结论。显然，没有单一的简单原则可以普遍适用。
• Photoleitende Flüssigkristalle aus der Reihe der 2,3,6,7-Tetrakis(alkoxy)triphenylene / Liquid Crystals in the Series of 2,3,6,7-Tetraalkoxytriphenylenes
  作者：Bernd Rose、Herbert Meier

  DOI：10.1515/znb-1998-0915

  日期：1998.9.1

  Stepwise bromination of the triphenylene 1 leads regioselectively to the monobromo and the dibromo compound 2 and 3, respectively (Scheme 1). In contrast to 1 and 2, the dibromo derivative 3 as well as the nitrile 4. obtained from 3 and CuCN, form thermotropic mesophases D_h. On irradiation of 3 and 4 a photocurrent can be measured in the crystalline state and an enhanced photocurrent in the LC phase.

  三苯基烯1的逐步溴化反应在区域选择性上导致了单溴化合物2和双溴化合物3（方案1）。与1和2相比，来自3和CuCN的双溴衍生物3以及腈4形成热致中间相Dh。在3和4的晶态下，辐照可以测量到光电流，而在LC相中可以获得增强的光电流。
• Meier, Herbert; Rose, Bernd, Journal fur Praktische Chemie - Chemiker-Zeitung, 1998, vol. 340, # 6, p. 536 - 543
  作者：Meier, Herbert、Rose, Bernd

  DOI：——

  日期：——
• Mixed Alkyl-Alkoxy Triphenylenes
  作者：Andrew N Cammidge、Hemant Gopee

  DOI：10.1080/714965603

  日期：2003.1
• Solution-Phase Dimerization of an Oblong Shape-Persistent Macrocycle
  作者：Meng Chu、Ashley N. Scioneaux、C. Scott Hartley

  DOI：10.1021/jo501260c

  日期：2014.10.3

  A new shape-persistent macrocycle comprising two 2,3-triphenylene moieties bridged by m-phenylene ethynylenes has been synthesized. UV-vis and fluorescence spectroscopies indicate limited interaction between the two triphenylene units. The compound, which has a pronounced oblong shape (the core measures approximately 2.2 X 1.0 nm), aggregates in CDCl3 and toluene-d(8) to give stacked dimers, as indicated by the H-1 NMR signals corresponding to protons on or near the core, which shift upfield with increasing concentration. These changes in NMR shielding were modeled using DFT calculations on candidate dimer geometries. The best match to the experimental data was obtained for a dimer consisting of arene-arene stacking by 3.6 angstrom (on average) with a displacement along the molecular long axis of 3.5-4.0 angstrom. This displacement is larger than can be explained by the electronic effects of aromatic stacking interactions. Instead, the minimization of steric interactions between the side chains appears to control the dimer geometry, with the alkoxy groups of one molecule sliding into registry with the gaps along the periphery of the other. Such lateral displacement (as opposed to rotation) is a direct consequence of the extended oval shape of the compound.