1-[4-[2,5-Dihexoxy-4-(2-phenylethynyl)phenyl]buta-1,3-diynyl]-2,5-dihexoxy-4-(2-phenylethynyl)benzene | 1422182-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[4-[2,5-Dihexoxy-4-(2-phenylethynyl)phenyl]buta-1,3-diynyl]-2,5-dihexoxy-4-(2-phenylethynyl)benzene
• 英文别名: 1-[4-[2,5-dihexoxy-4-(2-phenylethynyl)phenyl]buta-1,3-diynyl]-2,5-dihexoxy-4-(2-phenylethynyl)benzene
• CAS: 1422182-17-9
• 化学式: C₅₆H₆₆O₄
• 分子量: 803.138
• InChiKey: DYVFWWLSXKWOAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.6
• 重原子数：
  60
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-ethynyl-2,5-bis(hexyloxy)-4-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四甲基乙二胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二异丙胺 、 三苯基膦 、 copper(l) chloride 作用下， 生成 1-[4-[2,5-Dihexoxy-4-(2-phenylethynyl)phenyl]buta-1,3-diynyl]-2,5-dihexoxy-4-(2-phenylethynyl)benzene
  参考文献：
  名称：

  Role of Hydrogen Bonding on the Self-Organization of Phenyleneethynylenes on Surfaces

  摘要：

  A series of carboxylic acid substituted phenyleneethynylenes, having a rigid backbone of 2.7 +/- 0.1 nm, were synthesized by following the Heck-Cassar-Sonagashira-Hagihara cross-coupling reaction. Hydrogen bonding, through the formation of cyclic dimers of carboxylic acid, is more preferred over catemeric structures in all the molecular systems under investigation. The formation of extended two-dimensional patterns on highly oriented pyrolitic graphite (HOPG) surface is dictated by the position as well as number of the carboxylic acid groups on the phenyleneethynylenes. Highly ordered extended arrangements, in the linear and stepwise fashion, were observed when the carboxylic acid groups are attached in the para and meta positions of phenyleneethynylenes. The vital role of the number of carboxylic acid on the organization of molecules is evident in the case of tetracarboxylic acid derivative wherein a Kagome-type structure was observed. Further, the coassembly of two types of phenyleneethynylenes was achieved on HOPG surface through acid base interaction.

  DOI：

  10.1021/la3048592

文献信息

• Role of Hydrogen Bonding on the Self-Organization of Phenyleneethynylenes on Surfaces
  作者：Pratap Zalake、K. George Thomas

  DOI：10.1021/la3048592

  日期：2013.2.19

  A series of carboxylic acid substituted phenyleneethynylenes, having a rigid backbone of 2.7 +/- 0.1 nm, were synthesized by following the Heck-Cassar-Sonagashira-Hagihara cross-coupling reaction. Hydrogen bonding, through the formation of cyclic dimers of carboxylic acid, is more preferred over catemeric structures in all the molecular systems under investigation. The formation of extended two-dimensional patterns on highly oriented pyrolitic graphite (HOPG) surface is dictated by the position as well as number of the carboxylic acid groups on the phenyleneethynylenes. Highly ordered extended arrangements, in the linear and stepwise fashion, were observed when the carboxylic acid groups are attached in the para and meta positions of phenyleneethynylenes. The vital role of the number of carboxylic acid on the organization of molecules is evident in the case of tetracarboxylic acid derivative wherein a Kagome-type structure was observed. Further, the coassembly of two types of phenyleneethynylenes was achieved on HOPG surface through acid base interaction.