4,4'-((((buta-1,3-diyne-1,4-diylbis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))bis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))diphenol | 1236051-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,4'-((((buta-1,3-diyne-1,4-diylbis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))bis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))diphenol
• CAS: 1236051-03-8
• 化学式: C₁₀₄H₁₂₂O₂
• 分子量: 1404.11
• InChiKey: XHLZDVRXFFRTIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.1
• 重原子数：
  106.0
• 可旋转键数：
  40.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4'-((((buta-1,3-diyne-1,4-diylbis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))bis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))diphenol 、 3-carboxy-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以55%的产率得到
  参考文献：
  名称：

  Flexibility of Shape-Persistent Molecular Building Blocks Composed of p-Phenylene and Ethynylene Units

  摘要：

  Ethynylene and p-phenylene are frequently employed constitutional units in constructing the backbone of nanoscopic molecules with specific shape and mechanical or electronic function. How well these properties are defined depends on the flexibility of the backbone, which can be characterized via the end-to-end distance distribution. This distribution is accessible by pulse electron paramagnetic resonance (EPR) distance measurements between spin labels that are attached at the backbone. Four sets of oligomer with different sequences of p-phenylene and ethynylene units and different spin labels were prepared using polar tagging as a tool for simple isolation of the targeted compounds. By variation of backbone length, of the sequence of p-phenylene and ethynylene units, and of the spin labels a consistent coarse-grained model for backbone flexibility of oligo(p-phenyleneethynylene)s and oligo(p-phenylenebutadiynylene)s is obtained. The relation of this harmonic segmented chain model to the worm-like chain model for shape-persistent polymers and to atomistic molecular dynamics simulations is discussed. Oligo(p-phenylene butadiynylene)s are found to be more flexible than oligo(p-phenyleneethynylene)s, but only slightly so. The end-to-end distance distribution measured in a glassy state of the solvent at a temperature of 50 K is found to depend on the glass transition temperature of the solvent. In the range between 91 and 373 K this dependence is in quantitative agreement with expectations for flexibility due to harmonic bending. For the persistence lengths at 298 K our data predict values of (13.8 +/- 1.5) nm for poly(p-phenyleneethynylene)s and of (11.8 +/- 1.5) nm for poly(p-phenylenebutadiynylene)s.

  DOI：

  10.1021/ja102983b
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.5h， 生成 4,4'-((((buta-1,3-diyne-1,4-diylbis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))bis(2,5-dihexyl-4,1-phenylene))bis(buta-1,3-diyne-4,1-diyl))diphenol
  参考文献：
  名称：

  Flexibility of Shape-Persistent Molecular Building Blocks Composed of p-Phenylene and Ethynylene Units

  摘要：

  Ethynylene and p-phenylene are frequently employed constitutional units in constructing the backbone of nanoscopic molecules with specific shape and mechanical or electronic function. How well these properties are defined depends on the flexibility of the backbone, which can be characterized via the end-to-end distance distribution. This distribution is accessible by pulse electron paramagnetic resonance (EPR) distance measurements between spin labels that are attached at the backbone. Four sets of oligomer with different sequences of p-phenylene and ethynylene units and different spin labels were prepared using polar tagging as a tool for simple isolation of the targeted compounds. By variation of backbone length, of the sequence of p-phenylene and ethynylene units, and of the spin labels a consistent coarse-grained model for backbone flexibility of oligo(p-phenyleneethynylene)s and oligo(p-phenylenebutadiynylene)s is obtained. The relation of this harmonic segmented chain model to the worm-like chain model for shape-persistent polymers and to atomistic molecular dynamics simulations is discussed. Oligo(p-phenylene butadiynylene)s are found to be more flexible than oligo(p-phenyleneethynylene)s, but only slightly so. The end-to-end distance distribution measured in a glassy state of the solvent at a temperature of 50 K is found to depend on the glass transition temperature of the solvent. In the range between 91 and 373 K this dependence is in quantitative agreement with expectations for flexibility due to harmonic bending. For the persistence lengths at 298 K our data predict values of (13.8 +/- 1.5) nm for poly(p-phenyleneethynylene)s and of (11.8 +/- 1.5) nm for poly(p-phenylenebutadiynylene)s.

  DOI：

  10.1021/ja102983b