1,6-bis(perfluorophenyl)-1,3,5-hexatriene | 1003605-52-4

• 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: 1,6-bis(perfluorophenyl)-1,3,5-hexatriene
• 英文别名: 1,2,3,4,5-pentafluoro-6-[(1E,3E,5E)-6-(2,3,4,5,6-pentafluorophenyl)hexa-1,3,5-trienyl]benzene
• CAS: 1003605-52-4
• 化学式: C₁₈H₆F₁₀
• 分子量: 412.23
• InChiKey: BJKDKKMTHFQCGG-CRQXNEITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,6-bis(perfluorophenyl)-1,3,5-hexatriene 生成
  参考文献：
  名称：

  [2+2] Photodimerization and photopolymerization of diphenylhexatriene crystals utilizing perfluorophenyl–phenyl stacking interactions

  摘要：

  Irradiation of the crystal of 1-perfluorophenyl-6-phenyl-1,3,5-hexatriene (1), the 1:1 cocrystal of 1,6diphenyl-1,3,5-hexatriene (2) and 1,6-bis(perfluorophenyl)-1,3,5-hexatriene (3) (2/3), and crystal 3 gave a mixture of dimer, trimer and higher oligomers that was soluble in common organic solvents. The highest molecular weight was 5000-8000 (the degree of polymerization = 15-20). The order of reactivity was 1 > 2/3 >> 3. The reaction of I was relatively efficient compared to typical organic crystals. The conversion reached 100% after 3 h irradiation. In each case, the regio- and stereoselectivity in the photodimerization was high, whereas in the formation of trimer and higher oligomers, the selectivity was much lower. The main dimer was spectroscopically identified to be the face-to-face dimer formed by the [2 + 2] cycloaddition at the 1,2-position of the triene double bonds. The photoproducts from 1 and 2/3 were amorphous, as evidenced by powder X-ray diffraction and polarizing optical microscopy. This is probably due to the nonplanar and bulky structures of the cyclobutane products. The photodimerization and polymerization are considered to be non-topochemical reactions. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.09.010

文献信息

• [2+2] Photodimerization and photopolymerization of diphenylhexatriene crystals utilizing perfluorophenyl–phenyl stacking interactions
  作者：Yoriko Sonoda、Midori Goto、Seiji Tsuzuki、Haruhisa Akiyama、Nobuyuki Tamaoki

  DOI：10.1016/j.jfluchem.2008.09.010

  日期：2009.2

  Irradiation of the crystal of 1-perfluorophenyl-6-phenyl-1,3,5-hexatriene (1), the 1:1 cocrystal of 1,6diphenyl-1,3,5-hexatriene (2) and 1,6-bis(perfluorophenyl)-1,3,5-hexatriene (3) (2/3), and crystal 3 gave a mixture of dimer, trimer and higher oligomers that was soluble in common organic solvents. The highest molecular weight was 5000-8000 (the degree of polymerization = 15-20). The order of reactivity was 1 > 2/3 >> 3. The reaction of I was relatively efficient compared to typical organic crystals. The conversion reached 100% after 3 h irradiation. In each case, the regio- and stereoselectivity in the photodimerization was high, whereas in the formation of trimer and higher oligomers, the selectivity was much lower. The main dimer was spectroscopically identified to be the face-to-face dimer formed by the [2 + 2] cycloaddition at the 1,2-position of the triene double bonds. The photoproducts from 1 and 2/3 were amorphous, as evidenced by powder X-ray diffraction and polarizing optical microscopy. This is probably due to the nonplanar and bulky structures of the cyclobutane products. The photodimerization and polymerization are considered to be non-topochemical reactions. (C) 2008 Elsevier B.V. All rights reserved.