4'',5''-bis(4-bromophenyl)-4,4''''-dimethoxy-3'',6''-diphenyl-1,1':4',1'':2'',1''':4''',1''''-quinquephenyl | 1033016-27-1

• 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: 4'',5''-bis(4-bromophenyl)-4,4''''-dimethoxy-3'',6''-diphenyl-1,1':4',1'':2'',1''':4''',1''''-quinquephenyl
• CAS: 1033016-27-1
• 化学式: C₅₆H₄₀Br₂O₂
• 分子量: 904.74
• InChiKey: ISLLNCGOMPLMAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.56
• 重原子数：
  60.0
• 可旋转键数：
  10.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4'',5''-bis(4-bromophenyl)-4,4''''-dimethoxy-3'',6''-diphenyl-1,1':4',1'':2'',1''':4''',1''''-quinquephenyl 、 1-hexadecylmagnesium bromide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以84%的产率得到4'',5''-bis(4-hexadecylphenyl)-4,4''''-dimethoxy-3'',6''-diphenyl-1,1':4',1'':2'',1''':4''',1''''-quinquephenyl
  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
• 作为产物：
  描述：

  bis-p-(p-anisyl)phenylacetylene 、 3,4-bis-(4-bromo-phenyl)-2,5-diphenyl-cyclopentadienone 以 二苯醚 为溶剂， 反应 23.0h， 以73%的产率得到4'',5''-bis(4-bromophenyl)-4,4''''-dimethoxy-3'',6''-diphenyl-1,1':4',1'':2'',1''':4''',1''''-quinquephenyl
  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