1,2-bis(4'-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-4-biphenylyl)ethyne | 862300-25-2

• 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: 1,2-bis(4'-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-4-biphenylyl)ethyne
• CAS: 862300-25-2
• 化学式: C₄₀H₄₆O₈
• 分子量: 654.8
• InChiKey: NWSSILSWGZECLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  48.0
• 可旋转键数：
  22.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(4'-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-4-biphenylyl)ethyne 在 dicobalt octacarbonyl 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以58%的产率得到1,2,3,4,5,6-Hexakis[4-[4-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]phenyl]benzene
  参考文献：
  名称：

  Ionic Conduction in Poly(ethylene glycol)-Functionalized Hexa-peri-hexabenzocoronene Amphiphiles

  摘要：

  Discotic liquid crystals based on hexa-peri-hexabenzocoronenes (HBCs) symmetrically substituted with six poly(ethylene glycol) (PEG) chains and further doped with LiCF3SO3 (LiTf) salt at different [EG]:[Li+] ratios nanophaseseparate in domains composed from HBC columns and PEG chains. These model amphiphiles behave as viscoelastic solids with a shear modulus of 5 X 10(6) Pa and an ionic conductivity of 10(-5) S/cm at 373 K. At temperatures below 333 K an ionic superstructure is formed of higher shear modulus (108 Pa) that surrounds the HBC columns and follows the disks in their rotational motion. However, the ionic superstructure impedes ion transport. Substituting the HBC core with two PEG chains breaks the symmetry of the ionic superstructure and increases ionic conductivity by an order of magnitude while retaining a high shear modulus and a viscoelastic response. These findings demonstrate that PEG-functionalized HBCs have great potential as new electrolytes because they combine ionic conductivity with mechanical stability. Moreover, when combined with electronic conduction within the HBC columns, this design can result in structures that exhibit simultaneous electronic and ionic transport.

  DOI：

  10.1021/acs.macromol.7b00224
• 作为产物：
  描述：

  4'-bromo-4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}biphenyl 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 苯 为溶剂， 反应 24.0h， 生成 1,2-bis(4'-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-4-biphenylyl)ethyne
  参考文献：
  名称：

  Ionic Conduction in Poly(ethylene glycol)-Functionalized Hexa-peri-hexabenzocoronene Amphiphiles

  摘要：

  Discotic liquid crystals based on hexa-peri-hexabenzocoronenes (HBCs) symmetrically substituted with six poly(ethylene glycol) (PEG) chains and further doped with LiCF3SO3 (LiTf) salt at different [EG]:[Li+] ratios nanophaseseparate in domains composed from HBC columns and PEG chains. These model amphiphiles behave as viscoelastic solids with a shear modulus of 5 X 10(6) Pa and an ionic conductivity of 10(-5) S/cm at 373 K. At temperatures below 333 K an ionic superstructure is formed of higher shear modulus (108 Pa) that surrounds the HBC columns and follows the disks in their rotational motion. However, the ionic superstructure impedes ion transport. Substituting the HBC core with two PEG chains breaks the symmetry of the ionic superstructure and increases ionic conductivity by an order of magnitude while retaining a high shear modulus and a viscoelastic response. These findings demonstrate that PEG-functionalized HBCs have great potential as new electrolytes because they combine ionic conductivity with mechanical stability. Moreover, when combined with electronic conduction within the HBC columns, this design can result in structures that exhibit simultaneous electronic and ionic transport.

  DOI：

  10.1021/acs.macromol.7b00224

文献信息

• Systematic Studies on Structural Parameters for Nanotubular Assembly of Hexa-<i>peri</i>-hexabenzocoronenes
  作者：Wusong Jin、Yohei Yamamoto、Takanori Fukushima、Noriyuki Ishii、Jungeun Kim、Kenichi Kato、Masaki Takata、Takuzo Aida

  DOI：10.1021/ja801179e

  日期：2008.7.1

  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.
• Semi-fused hexaphenyl hexa-peri-hexabenzocoronene: a novel fluorophore from an intramolecular Scholl reaction
  作者：Yunyi Lu、Jeffrey S. Moore

  DOI：10.1016/j.tetlet.2009.04.103

  日期：2009.7

  A semi-fused hexaphenyl hexabenzocoronene derivative (hexaphenyl-1/2HBC) was discovered and isolated from an intramolecular Scholl reaction of an oligo(ethyleneglycol) substituted hexabiphenylbenzene. This new derivative exhibits blue-shifted lambda(em) and significantly enhanced fluorescence in dichloromethane compared to the completely cyclized hexaphenyl-HBC derivative. (C) 2009 Elsevier Ltd. All rights reserved.