4,4''-bis(trimethylsilyl)-4',5'-diethyl-o-terphenyl | 1040726-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4''-bis(trimethylsilyl)-4',5'-diethyl-o-terphenyl
• CAS: 1040726-00-8
• 化学式: C₂₈H₃₈Si₂
• 分子量: 430.781
• InChiKey: OZOVIOYAFSBRIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.24
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4,4''-bis(trimethylsilyl)-4',5'-diethyl-o-terphenyl 在 一氯化碘 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到4,4''-diiodo-4',5'-diethyl-o-terphenyl
  参考文献：
  名称：

  Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-Transfer Oxidation of Lipshutz Cuprates and Formation of Nanostructural Materials from Hexadodecyloxynonaphenylene

  摘要：

  Nonaphenylenes and dodecaphenylenes have been synthesized by using electron-transfer oxidation of Lipshutz cuprates with duroquinone. Oxidation of the Lipshutz cuprate derived from 4,4"-dibromo-o-terphenyl 3a in THF produced nonaphenylene la in 46% yield, whereas the similar oxidation of the Lipshutz cuprates derived from 4,4"-diiodo-4',5'-dialkyl-o-terphenyls 3b-d in ether afforded the corresponding nonaphenylenes 1b-d and dodecaphenylenes. 2b-d in moderate total yields. In the case of 4,4"-diiodo-4',5'-didodecyloxy-o-terphenyl 3e as the starting material, oxidation of the corresponding Lipshutz cuprate in ether or THF only led to the formation of nonaphenylene le. Both nonaphenylenes 1a-e and dodecaphenylenes 2b-d are unreactive to fight, atmospheric oxygen, and prolonged heating. These oligophenylenes showed strong UV absorption and fluorescent emission and exhibited some redox properties on CV analysis. Moreover, hexadodecyloxyrionaphenylene le exhibits different nanostructures on the surface and in solution to form a film by casting a solution of 1e in cyclohexane, benzene, chloroform, THF, or diisopropyl ether (EPE) and nanofibers from IPE-MeOH (1: 1), indicating different absorption and emission spectra and XRD patterns. The absorption maxima of THF solution, fiber, and film are in the order of le film (315 nm) > fiber (302 nm) > solution (295 ran), whereas the emission maxima are in the order of 1e fiber (425 m) > solution (418 nm) > film (401 nm). XRD analysis revealed that le aligns laterally on a glass or silicon surface to form a thin film with a lamella structure; however, it forms a nanofiber with a Lego-like stacking structure without pi-pi stacking interaction of the aromatic rings. Reflecting the different nanostructures of the 1e film and fiber, a spin-coated le film is found to be effective in detecting the vapor of explosives due to the intercalation of nitroaromatics to the cracked surface of the loosely stacked 1e. In contrast, the 1e fiber is not effective in detection of nitroaromatics but exhibits fluorescence anisotropy. The maximum fluorescence intensity is obtained in a direction perpendicular to the logitudinal axis of the fiber, indicating the stacking direction to be parallel to the longitudinal axis of the fiber.

  DOI：

  10.1021/jo800787u
• 作为产物：
  描述：

  4,5-diethyl-1,2-diodobenzene 、 1-溴-4-(三甲基硅基)苯 在 dichloro[1,3-bis(diphenylphosphino)propane]Ni(II) magnesium 作用下， 以 乙醚 为溶剂， 反应 49.0h， 以54%的产率得到4,4''-bis(trimethylsilyl)-4',5'-diethyl-o-terphenyl
  参考文献：
  名称：

  Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-Transfer Oxidation of Lipshutz Cuprates and Formation of Nanostructural Materials from Hexadodecyloxynonaphenylene

  摘要：

  Nonaphenylenes and dodecaphenylenes have been synthesized by using electron-transfer oxidation of Lipshutz cuprates with duroquinone. Oxidation of the Lipshutz cuprate derived from 4,4"-dibromo-o-terphenyl 3a in THF produced nonaphenylene la in 46% yield, whereas the similar oxidation of the Lipshutz cuprates derived from 4,4"-diiodo-4',5'-dialkyl-o-terphenyls 3b-d in ether afforded the corresponding nonaphenylenes 1b-d and dodecaphenylenes. 2b-d in moderate total yields. In the case of 4,4"-diiodo-4',5'-didodecyloxy-o-terphenyl 3e as the starting material, oxidation of the corresponding Lipshutz cuprate in ether or THF only led to the formation of nonaphenylene le. Both nonaphenylenes 1a-e and dodecaphenylenes 2b-d are unreactive to fight, atmospheric oxygen, and prolonged heating. These oligophenylenes showed strong UV absorption and fluorescent emission and exhibited some redox properties on CV analysis. Moreover, hexadodecyloxyrionaphenylene le exhibits different nanostructures on the surface and in solution to form a film by casting a solution of 1e in cyclohexane, benzene, chloroform, THF, or diisopropyl ether (EPE) and nanofibers from IPE-MeOH (1: 1), indicating different absorption and emission spectra and XRD patterns. The absorption maxima of THF solution, fiber, and film are in the order of le film (315 nm) > fiber (302 nm) > solution (295 ran), whereas the emission maxima are in the order of 1e fiber (425 m) > solution (418 nm) > film (401 nm). XRD analysis revealed that le aligns laterally on a glass or silicon surface to form a thin film with a lamella structure; however, it forms a nanofiber with a Lego-like stacking structure without pi-pi stacking interaction of the aromatic rings. Reflecting the different nanostructures of the 1e film and fiber, a spin-coated le film is found to be effective in detecting the vapor of explosives due to the intercalation of nitroaromatics to the cracked surface of the loosely stacked 1e. In contrast, the 1e fiber is not effective in detection of nitroaromatics but exhibits fluorescence anisotropy. The maximum fluorescence intensity is obtained in a direction perpendicular to the logitudinal axis of the fiber, indicating the stacking direction to be parallel to the longitudinal axis of the fiber.

  DOI：

  10.1021/jo800787u