1-Octyl-4-[4-[4-(1-octylpyridin-4-ylidene)cyclohexa-2,5-dien-1-ylidene]cyclohexa-2,5-dien-1-ylidene]pyridine | 872042-65-4

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 醌二甲烷类
• 英文名称: 1-Octyl-4-[4-[4-(1-octylpyridin-4-ylidene)cyclohexa-2,5-dien-1-ylidene]cyclohexa-2,5-dien-1-ylidene]pyridine
• 英文别名: 1-octyl-4-[4-[4-(1-octylpyridin-4-ylidene)cyclohexa-2,5-dien-1-ylidene]cyclohexa-2,5-dien-1-ylidene]pyridine
• CAS: 872042-65-4
• 化学式: C₃₈H₅₀N₂
• 分子量: 534.828
• InChiKey: LCMGKXKDNZXNIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Octyl-4-[4-[4-(1-octylpyridin-4-ylidene)cyclohexa-2,5-dien-1-ylidene]cyclohexa-2,5-dien-1-ylidene]pyridine 在 碘 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Synthesis and Characterization of a Highly Reducing Neutral “Extended Viologen” and the Isostructural Hydrocarbon 4,4‘ ‘‘ ‘-Di-n-octyl-p-quaterphenyl

  摘要：

  The molecule 4,4""-di-n-octyl-p-quaterphenyl was synthesized in one step by a nickel-catalyzed cross-coupling reaction. Powder X-ray diffraction shows that it crystallizes in a layered structure with the long axis of the molecule nearly perpendicular to the layer plane. Differential scanning calorimetry indicates a transition to a liquid-crystalline phase at 81 degrees C. Reaction of 4,4'-bis(4-pyridyl)biphenyl with 1-bromooctane yields the dication 2(2+)2Br(-), an "extended viologen" isostructural with 4,4""-di-n-octyl-p-quaterphenyl. Reduction of 2(2+)2Br(-) with sodium amalgam in DMF yields 2, the first neutral extended viologen to be isolated. The molecule 2 is, to the best of our knowledge, the most reducing neutral organic molecule that has, been synthesized. Single-crystal X-ray diffraction shows that a diradical form, either singlet or triplet, makes an important contribution to the electronic structure of 2. The broadened H-1 NMR spectrum of 2 indicates the presence of a triplet, but it has not been possible to observe the triplet by ESR spectroscopy. The electronic structure of 2 appears to be closely related to that of a classic molecule, Chichibabin's hydrocarbon.

  DOI：

  10.1021/ja053084q
• 作为产物：
  描述：

  在 sodium amalgam 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以68%的产率得到1-Octyl-4-[4-[4-(1-octylpyridin-4-ylidene)cyclohexa-2,5-dien-1-ylidene]cyclohexa-2,5-dien-1-ylidene]pyridine
  参考文献：
  名称：

  Synthesis and Characterization of a Highly Reducing Neutral “Extended Viologen” and the Isostructural Hydrocarbon 4,4‘ ‘‘ ‘-Di-n-octyl-p-quaterphenyl

  摘要：

  The molecule 4,4""-di-n-octyl-p-quaterphenyl was synthesized in one step by a nickel-catalyzed cross-coupling reaction. Powder X-ray diffraction shows that it crystallizes in a layered structure with the long axis of the molecule nearly perpendicular to the layer plane. Differential scanning calorimetry indicates a transition to a liquid-crystalline phase at 81 degrees C. Reaction of 4,4'-bis(4-pyridyl)biphenyl with 1-bromooctane yields the dication 2(2+)2Br(-), an "extended viologen" isostructural with 4,4""-di-n-octyl-p-quaterphenyl. Reduction of 2(2+)2Br(-) with sodium amalgam in DMF yields 2, the first neutral extended viologen to be isolated. The molecule 2 is, to the best of our knowledge, the most reducing neutral organic molecule that has, been synthesized. Single-crystal X-ray diffraction shows that a diradical form, either singlet or triplet, makes an important contribution to the electronic structure of 2. The broadened H-1 NMR spectrum of 2 indicates the presence of a triplet, but it has not been possible to observe the triplet by ESR spectroscopy. The electronic structure of 2 appears to be closely related to that of a classic molecule, Chichibabin's hydrocarbon.

  DOI：

  10.1021/ja053084q

文献信息

• Synthesis and Characterization of a Highly Reducing Neutral “Extended Viologen” and the Isostructural Hydrocarbon 4,4‘ ‘‘ ‘-Di-<i>n</i>-octyl-<i>p</i>-quaterphenyl
  作者：William W. Porter、Thomas P. Vaid、Arnold L. Rheingold

  DOI：10.1021/ja053084q

  日期：2005.11.30

  The molecule 4,4""-di-n-octyl-p-quaterphenyl was synthesized in one step by a nickel-catalyzed cross-coupling reaction. Powder X-ray diffraction shows that it crystallizes in a layered structure with the long axis of the molecule nearly perpendicular to the layer plane. Differential scanning calorimetry indicates a transition to a liquid-crystalline phase at 81 degrees C. Reaction of 4,4'-bis(4-pyridyl)biphenyl with 1-bromooctane yields the dication 2(2+)2Br(-), an "extended viologen" isostructural with 4,4""-di-n-octyl-p-quaterphenyl. Reduction of 2(2+)2Br(-) with sodium amalgam in DMF yields 2, the first neutral extended viologen to be isolated. The molecule 2 is, to the best of our knowledge, the most reducing neutral organic molecule that has, been synthesized. Single-crystal X-ray diffraction shows that a diradical form, either singlet or triplet, makes an important contribution to the electronic structure of 2. The broadened H-1 NMR spectrum of 2 indicates the presence of a triplet, but it has not been possible to observe the triplet by ESR spectroscopy. The electronic structure of 2 appears to be closely related to that of a classic molecule, Chichibabin's hydrocarbon.