1,2-bis(2,4-dimethyl-5,2':5',2''-terthiophen-3-yl)perfluorocyclopentene | 197302-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 1,2-bis(2,4-dimethyl-5,2':5',2''-terthiophen-3-yl)perfluorocyclopentene
• 英文别名: 3-[2-[2,4-Dimethyl-5-(5-thiophen-2-ylthiophen-2-yl)thiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2,4-dimethyl-5-(5-thiophen-2-ylthiophen-2-yl)thiophene；3-[2-[2,4-dimethyl-5-(5-thiophen-2-ylthiophen-2-yl)thiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2,4-dimethyl-5-(5-thiophen-2-ylthiophen-2-yl)thiophene
• CAS: 197302-78-6
• 化学式: C₃₃H₂₂F₆S₆
• 分子量: 724.924
• InChiKey: AUTXWIXDXQWDRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  667.3±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2-bis(2,4-dimethyl-5,2':5',2''-terthiophen-3-yl)perfluorocyclopentene 在 碘 、 碘酸 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以63%的产率得到1,2-bis(5''-iodo-2,4-dimethyl-5,2':5',2''-terthiophen-3-yl)perfluorocyclopentene
  参考文献：
  名称：

  Photochromism of diarylethenes having thiophene oligomers as the aryl groups

  摘要：

  Diarylperfluorocyclopentenes having thiophene oligomers as the aryl groups were synthesized and their photochromic reactivity was examined. The cylization quantum yields were scarcely affected by the oligomer chain length, while the ring-opening quantum yields dramatically decreased with the increasing number of the thiophene rings, The low quantum yield of a 1,2-bis(5 ''-cyano-2,4-dimethyl-5,2':5',2 ''-terthiophen-3-yl)perfluorocyclopentene closed-ring form was increased as large as 34 times by raising the reaction temperature from 25 degrees C to 150 degrees C. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00558-9
• 作为产物：
  描述：

  3-[2-(2,4-二甲基噻吩-3-基)-3,3,4,4,5,5-六氟环戊烯-1-基]-2,4-二甲基噻吩 在 碘 、 碘酸 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 1,2-bis(2,4-dimethyl-5,2':5',2''-terthiophen-3-yl)perfluorocyclopentene
  参考文献：
  名称：

  Photochromism of diarylethenes having thiophene oligomers as the aryl groups

  摘要：

  Diarylperfluorocyclopentenes having thiophene oligomers as the aryl groups were synthesized and their photochromic reactivity was examined. The cylization quantum yields were scarcely affected by the oligomer chain length, while the ring-opening quantum yields dramatically decreased with the increasing number of the thiophene rings, The low quantum yield of a 1,2-bis(5 ''-cyano-2,4-dimethyl-5,2':5',2 ''-terthiophen-3-yl)perfluorocyclopentene closed-ring form was increased as large as 34 times by raising the reaction temperature from 25 degrees C to 150 degrees C. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00558-9

文献信息

• Femtosecond Spectroscopic Study on Photochromic Diarylethenes with Terthiophene
  作者：N. Ohtaka、Y. Hase、K. Uchida、M. Irie、N. Tamai

  DOI：10.1080/10587250008023818

  日期：2000.6.1

  Photochromic ring-closure reactions of diarylethene derivatives with terthiophene (T3H, T3Me) have been examined by femtosecond transient absorption spectroscopy. The rate of the ring-closure reaction of T3H in n-hexane was estimated to be similar to 2.5 ps, which is very similar to that of T3Me in the same solvent. It was suggested that the ring-closure reaction proceeds through a concerted mechanism without any intermediates but not a two-step mechanism. The rate of ring-closure reaction was also dependent on the solvent polarity, suggesting that the charge transfer state in the excited singlet state plays an important role in the photochromic reaction.