2,3-bis(4'-hydroxy-4-biphenyl)-5,6-di(4-dodecylphenyl)-1,4-diphenylbenzene | 886209-38-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,3-bis(4'-hydroxy-4-biphenyl)-5,6-di(4-dodecylphenyl)-1,4-diphenylbenzene
• 英文别名: 4-[4-[4,5-Bis(4-dodecylphenyl)-2-[4-(4-hydroxyphenyl)phenyl]-3,6-diphenylphenyl]phenyl]phenol
• CAS: 886209-38-7
• 化学式: C₇₈H₈₆O₂
• 分子量: 1055.54
• InChiKey: YANBWQAGNWFIGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.6
• 重原子数：
  80
• 可旋转键数：
  30
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis(4'-hydroxy-4-biphenyl)-5,6-di(4-dodecylphenyl)-1,4-diphenylbenzene 、 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以68%的产率得到
  参考文献：
  名称：

  附有冠醚的六苯并萘石墨纳米线圈：主客体相互作用诱导的超分子手性。

  摘要：

  我们设计并合成了两种新的非手性六周六苯并冠状烯 (HBC) 衍生物 HBCCE 和 HBCTEG-CE，它们带有冠醚作为氨基酸结合位点的垂饰。HBCCE 自组装成 P 手和 M 手螺旋纳米线圈的外消旋混合物，然而，在手性氨基酸客体存在的情况下，它形成了具有单手螺旋感的螺旋纳米线圈。还研究了 HBCCE 与手性氨基酸共组装过程中客体的浓度、类型和构型对诱导圆二色性 (ICD) 的影响。此外，在完全去除手性客体后，即使存在具有相反构型的过量氨基酸，光学活性纳米线圈也不会外消旋化。相比之下，

  DOI：

  10.1002/chem.201904291
• 作为产物：
  描述：

  1,2-Bis(4-dodecylphenyl)-4,5-bis[4-(4-methoxyphenyl)phenyl]-3,6-diphenylbenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2,3-bis(4'-hydroxy-4-biphenyl)-5,6-di(4-dodecylphenyl)-1,4-diphenylbenzene
  参考文献：
  名称：

  Systematic Studies on Structural Parameters for Nanotubular Assembly of Hexa-peri-hexabenzocoronenes

  摘要：

  Thirteen different hexa-peri-hexabenzocoronenes (HBCs) I-III were newly synthesized, and their self-assembling behaviors were investigated. Taking into account also the reported behaviors of amphiphilic HBCs, some structural parameters of HBC essential for the tubular assembly were revealed. Points to highlight include (1) the importance of two phenyl groups attached to one side of the HBC unit, (2) essential roles of long paraffinic side chains on the other side of the phenyl groups, and (3) no necessity of hydrophilic oligo(ethylene glycol) side chains. The hierarchical nanotubular structure, rendered by virtue of a synchrotron radiation technique, was virtually identical to our previous proposal, where the nanotubes are composed of helically coiled bilayer tapes with a tilting angle of similar to 45 degrees. Each tape consists of pi-stacked HBC units, where the inner and outer HBC layers are connected by interdigitation of paraffinic side chains. The coiled structure is most likely caused by a steric congestion of the phenyl groups attached to the HBC unit, whose tilting direction may determine the handedness of the helically chiral nanotube.

  DOI：

  10.1021/ja801179e

文献信息

• Photochemical Stitching of a Tubularly Assembled Hexabenzocoronene Amphiphile by Dimerization of Coumarin Pendants
  作者：Jin Motoyanagi、Takanori Fukushima、Noriyuki Ishii、Takuzo Aida

  DOI：10.1021/ja060593z

  日期：2006.4.5

  lambda > 300 nm, the nanotubes in the solid state and suspension both underwent dimerization of the coumarin pendants, affording covalently stitched nanotubes, which were hardly soluble in CHCl3, a good solvent of 1. In contrast, a thin film cast from a homogeneous solution of 1 was intact to photoirradiation. Owing to the reversible nature of the photochemical stitching, both negative and positive

  一种添加香豆素的两亲性六邻六苯并可酮 (1) 自组装形成石墨纳米管。在 λ > 300 nm 的照射下，固态和悬浮液中的纳米管都经历了香豆素悬垂物的二聚化，得到共价缝合的纳米管，它们几乎不溶于 CHCl3，一种良好的溶剂 1。相比之下，从1 的均匀溶液对光辐照是完整的。由于光化学缝合的可逆性质，石墨纳米管的负图案和正图案均通过光刻后处理在硅基板上显影。
• Selective Synthesis of Single- and Multi-Walled Supramolecular Nanotubes by Using Solvophobic/Solvophilic Controls: Stepwise Radial Growth via “Coil-on-Tube” Intermediates
  作者：Seelam Prasanthkumar、Wei Zhang、Wusong Jin、Takanori Fukushima、Takuzo Aida

  DOI：10.1002/anie.201505806

  日期：2015.9.14

  solvated in C6F6 (solvophilic effect) and do not assemble, whereas in CH2Cl2, they are excluded (solvophobic effect) and assemble together consequently. For example, the use of C6F6 and CH2Cl2 as assembling media for FHBC leads to the selective formation of single‐ and multi‐walled nanotubes, respectively. When a higher monomer concentration is applied in CH2Cl2, multi‐walled nanotubes with a larger number

  新颖六围-hexabenzocoronene（HBC）衍生物，˚F HBC和˚F HBC *，这进行HBC芯和在另一长链烷基的尾部的一侧全氟烷片段，合成的。它们的全氟烷基链段在C 6 F 6中高度溶剂化（亲溶剂作用）并且不组装，而在CH 2 Cl 2中，它们被排除（疏溶剂作用）并因此组装在一起。例如，使用C 6 F 6和CH 2 Cl 2作为F的组装介质HBC分别选择性地形成了单壁和多壁纳米管。当在CH 2 Cl 2中使用较高的单体浓度时，会产生壁数较大的多壁纳米管。CH 2 Cl 2中的F HBC自组装相当缓慢，因此可以观察线圈上的结构，这可能是纳米管壁逐步放射状生长的中间产物。将多壁纳米管浇铸到石英板上会产生超疏水薄膜，水接触角为161±2°。
• Controlled Self-Assembly Triggered by Olefin Metathesis:  Cross-Linked Graphitic Nanotubes from an Amphiphilic Hexa-<i>p</i><i>eri</i>-hexabenzocoronene
  作者：Wusong Jin、Takanori Fukushima、Atsuko Kosaka、Makiko Niki、Noriyuki Ishii、Takuzo Aida

  DOI：10.1021/ja051859p

  日期：2005.6.1

  Acyclic diene metathesis (ADMET) in CH2Cl2 of a Gemini-shaped nonionic hexabenzocoronene amphiphile (2), bearing triethylene glycol chains with terminal allylic functionalities, resulted in spontaneous formation of graphitic nanotubes with a cross-linked surface. Without ADMET, 2 did not self-assemble to form a tubular structure due to a high solubility in CH2Cl2. Although 2 formed nanotubes in THF, ADMET on the surface of the preformed nanotubes in THF proceeded only sluggishly and resulted in partial disruption of the tubular structure. The cross-linked nanotubes showed a softening temperature (244 degrees C) higher than that of the uncross-linked version (195 degrees C) and preserved their hollow structure much longer upon heating.
• Stabilization of a Kinetically Favored Nanostructure:  Surface ROMP of Self-Assembled Conductive Nanocoils from a Norbornene-Appended Hexa-<i>p</i><i>eri</i>-hexabenzocoronene
  作者：Takuya Yamamoto、Takanori Fukushima、Yohei Yamamoto、Atsuko Kosaka、Wusong Jin、Noriyuki Ishii、Takuzo Aida

  DOI：10.1021/ja064461h

  日期：2006.11.1

  Newly designed norbornene-appended hexabenzocoronene 1 self-assembles, upon diffusion of an Et2O vapor into its CH2Cl2 solution, to form either graphitic nanocoils or nanotubes, depending on the self-assembling conditions. The coiled assembly, selectively formed at 15 degrees C, is a kinetic intermediate for the tubular assembly and transforms into nanotubes on standing at 25 degrees C. However, post-ring-opening metathesis polymerization of the norbornene pendants of 1 enhances the thermal stability of the coiled assembly as well as the tubular one and disables a thermodynamic coil-to-tube transition. The polymerized nanocoils show an electroconductivity of 1 x 10(-4) S cm(-1) upon doping with I-2, while the nonpolymerized nanocoils are disrupted upon being doped.