1,4-bis(4-bromophenyl)-2,3,5,6-tetrakis[4-(3,7-dimethyloctyl)phenyl]benzene | 816466-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-bis(4-bromophenyl)-2,3,5,6-tetrakis[4-(3,7-dimethyloctyl)phenyl]benzene
• CAS: 816466-80-5
• 化学式: C₈₂H₁₀₈Br₂
• 分子量: 1253.57
• InChiKey: YFTZTXNJZYDMPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.79
• 重原子数：
  84.0
• 可旋转键数：
  34.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  异丙醇频哪醇硼酸酯 、 1,4-bis(4-bromophenyl)-2,3,5,6-tetrakis[4-(3,7-dimethyloctyl)phenyl]benzene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到4,4,5,5-Tetramethyl-2-[4-[2,3,5,6-tetrakis[4-(3,7-dimethyloctyl)phenyl]-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]phenyl]-1,3,2-dioxaborolane
  参考文献：
  名称：

  Two-Dimensional Graphene Nanoribbons

  摘要：

  A new synthetic strategy toward novel linear two-dimensional graphene nanoribbons up to 12 nm has been established. The nanoribbons are characterized by MS, UV/vis, and scanning tunneling microscopy (STM). Various microscopic studies of these novel structures showed a high tendency to self-assemble.

  DOI：

  10.1021/ja710234t
• 作为产物：
  描述：

  4-(3,7-dimethyloctyl)phenyl magnesium bromide 在 四(三苯基膦)钯 、 碘 、 甲基三辛基氯化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 64.0h， 生成 1,4-bis(4-bromophenyl)-2,3,5,6-tetrakis[4-(3,7-dimethyloctyl)phenyl]benzene
  参考文献：
  名称：

  Synthesis, characterization, and DFT study of polycyclic aromatic hydrocarbon precursors, 1,4-diiodo-2,3,5,6-tetraarylbenzene and 1,4-bis(4-bromophenyl)-2,3,5,6-tetraarylbenzene

  摘要：

  The molecular structure and spectroscopic properties of 1,4-diiodo-2,3,5,6-tetraarylbenzene and 1,4-bis(4-bromophenyl)-2,3,5,6-tetraarylbenzene have been investigated by density functional theory (DFT), H-1 NMR, C-13 NMR, IR spectroscopy, and elemental analysis. These compounds are the precursors for the synthesis of large polycyclic aromatic hydrocarbons (PAHs). Because of the flexibility of aliphatic chains, DFT calculations of C-13 NMR chemical shifts were only calculated in the aromatic region by introducing H atoms replacing the aliphatic chains and H-1 NMR chemical shifts were neglected. A drawback of excluding aliphatic chains in the IR calculation was the loss of vibrational modes for C-H stretching and bending. Due to this significant loss of information, the aliphatic chains were included in the IR calculations. The comparison of the calculated C-13 NMR and IR parameters with the experimental spectroscopic data reveals good agreement and thus confirmed the suggested molecular structures. In addition, the electronic structure of these compounds was discussed based on HOMO-LUMO analyses. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.07.033

文献信息

• Alternating Donor-Acceptor Arrays from Hexa-peri-hexabenzocoronene and Benzothiadiazole: Synthesis, Optical Properties, and Self-Assembly
  作者：Felix Hinkel、Don Cho、Wojciech Pisula、Martin Baumgarten、Klaus Müllen

  DOI：10.1002/chem.201403111

  日期：2015.1.2

  Donor–acceptor (D–A) structures were obtained by alternating arrays of hexa‐peri‐hexabenzocoronene (HBC) and benzo[c][1,2,5]thiadiazole (BTZ). Optoelectronic investigations revealed a charge transfer due to strong push–pull interactions. 2 D wide‐angle X‐ray scattering (WAXS) data indicated an arrangement in liquid‐crystalline columnar assemblies, in which the π‐stacking distances and molecular orientation

  供体-受体（D–A）结构是通过交替排列的六-peri-hexabenzocoronene（HBC）和苯并[ c ] [1,2,5]噻二唑（BTZ）获得的。光电研究表明，由于强烈的推挽相互作用，电荷转移。2 D广角X射线散射（WAXS）数据表明液晶柱状组件中的排列，其中π堆积距离和分子取向取决于分子中HBC单元的数量。
• Oligomers of Hexa-<i>p</i><i>eri</i>-hexabenzocoronenes as “Super-oligophenylenes”:  Synthesis, Electronic Properties, and Self-assembly
  作者：Jishan Wu、Mark D. Watson、Natalia Tchebotareva、Zhaohui Wang、Klaus Müllen

  DOI：10.1021/jo0490301

  日期：2004.11.1

  Hexa-peri-hexabenzocoronene (HBC) is a remarkable polycyclic aromatic hydrocarbon and is often called "superbenzene" because of its similarity to benzene. In this article we present the facile synthesis of oligomers of HBC, up to trimers (3, 4, 5a-c) with different modes of connection. UV-vis and fluorescence spectroscopy studies reveal that the oligomers are electronically decoupled. This arises from the small atomic orbital coefficients of the bridge-head carbon atoms, the large torsion angle between the HBC units, and the large distance of interacting transition dipoles due to the size of the HBC chromophore. For comparison, a methylene-bridged HBC dimer 6, so-called "superfluorene", was prepared. The induced planarity improves pi-conjugation and suppresses the geometrical relaxation of the backbone upon electronic excitation, leading to a prominent 0-0 transition band in the fluorescence spectra. The self-assembly of the oligomers and of superfluorene 6 was studied by wide-angle X-ray diffraction (WAXD) in the bulk state, and ordered columnar stacking occurs in the HBC dimer 3, p-HBC trimer 4, and superfluorene 6. Measurements of shear-aligned samples show that, despite increasing aspects ratio by linear entrainment of disks, the anitropic element that is subject to alignment by shear is the supramolecular columns.