1-[2,4-dimethyl-5-phenyl-3-thienyl]-2-[4-methyl-2,5-bis(trimethylsilylethynyl)-3-thienyl]hexafluorocyclopentene | 868389-62-2

• 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-[2,4-dimethyl-5-phenyl-3-thienyl]-2-[4-methyl-2,5-bis(trimethylsilylethynyl)-3-thienyl]hexafluorocyclopentene
• 英文别名: 2-[3-[2-(2,4-Dimethyl-5-phenylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-4-methyl-5-(2-trimethylsilylethynyl)thiophen-2-yl]ethynyl-trimethylsilane；2-[3-[2-(2,4-dimethyl-5-phenylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-4-methyl-5-(2-trimethylsilylethynyl)thiophen-2-yl]ethynyl-trimethylsilane
• CAS: 868389-62-2
• 化学式: C₃₂H₃₂F₆S₂Si₂
• 分子量: 650.899
• InChiKey: ZOTKWQADKXGEJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.69
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[2,4-dimethyl-5-phenyl-3-thienyl]-2-[4-methyl-2,5-bis(trimethylsilylethynyl)-3-thienyl]hexafluorocyclopentene 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 sodium periodate 、 copper(l) iodide 、 air 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 24.0h， 生成 1-[2,4-dimethyl-5-phenyl-3-thienyl]-2-[4-methyl-2,5-bis(5-(1-oxyl-3-oxide-4,4,5,5-tetramethylimidazolin-2-yl)thienylethynyl)-3-thienyl]hexafluorocyclopentene
  参考文献：
  名称：

  New Photoswitching Unit for Magnetic Interaction:  Diarylethene with 2,5-Bis(arylethynyl)-3-thienyl Group

  摘要：

  Photoswitching of the intramolecular magnetic interaction was demonstrated using diarylethenes with 2,5-bis(arylethynyl)-4-methyi-3-thienyl side group. Two nitroxide radicals were placed at each end of the 2,5-bis(arylethynyl)-4-methyl-3-thienyI group. Three kinds of aryl groups, 2,5-thienylene, p-phenylene, and m-phenylene groups, were used in the arylethynyl moiety. The diarylethene photoswitching units have an extended pi-conjugated chain on one side of the diarylethene. The photochromic reactivity was dependent on the arylethynyl group. Diarylethenes with m-phenylene group showed an efficient photochromic reactivity. Along with the photochromic reaction the diarylethenes showed photoswitching of an ESR spectrum originating from the change in the magnetic interaction between two unpaired electrons. The open-ring isomer showed stronger exchange interaction than the photogenerated closed-ring isomer. The magnetic interaction between two radicals via the pi-conjugated chain was altered by photocyclization due to the change of the hybrid orbital at the 2-position of the thiophene ring from sp(2) to sp(3).

  DOI：

  10.1021/ja053200p
• 作为产物：
  描述：

  3-bromo-4-methyl-2,5-bis(trimethylsilylethynyl)thiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 1-[2,4-dimethyl-5-phenyl-3-thienyl]-2-[4-methyl-2,5-bis(trimethylsilylethynyl)-3-thienyl]hexafluorocyclopentene
  参考文献：
  名称：

  New Photoswitching Unit for Magnetic Interaction:  Diarylethene with 2,5-Bis(arylethynyl)-3-thienyl Group

  摘要：

  Photoswitching of the intramolecular magnetic interaction was demonstrated using diarylethenes with 2,5-bis(arylethynyl)-4-methyi-3-thienyl side group. Two nitroxide radicals were placed at each end of the 2,5-bis(arylethynyl)-4-methyl-3-thienyI group. Three kinds of aryl groups, 2,5-thienylene, p-phenylene, and m-phenylene groups, were used in the arylethynyl moiety. The diarylethene photoswitching units have an extended pi-conjugated chain on one side of the diarylethene. The photochromic reactivity was dependent on the arylethynyl group. Diarylethenes with m-phenylene group showed an efficient photochromic reactivity. Along with the photochromic reaction the diarylethenes showed photoswitching of an ESR spectrum originating from the change in the magnetic interaction between two unpaired electrons. The open-ring isomer showed stronger exchange interaction than the photogenerated closed-ring isomer. The magnetic interaction between two radicals via the pi-conjugated chain was altered by photocyclization due to the change of the hybrid orbital at the 2-position of the thiophene ring from sp(2) to sp(3).

  DOI：

  10.1021/ja053200p

文献信息

• New Photoswitching Unit for Magnetic Interaction:  Diarylethene with 2,5-Bis(arylethynyl)-3-thienyl Group
  作者：Naoki Tanifuji、Masahiro Irie、Kenji Matsuda

  DOI：10.1021/ja053200p

  日期：2005.9.28

  Photoswitching of the intramolecular magnetic interaction was demonstrated using diarylethenes with 2,5-bis(arylethynyl)-4-methyi-3-thienyl side group. Two nitroxide radicals were placed at each end of the 2,5-bis(arylethynyl)-4-methyl-3-thienyI group. Three kinds of aryl groups, 2,5-thienylene, p-phenylene, and m-phenylene groups, were used in the arylethynyl moiety. The diarylethene photoswitching units have an extended pi-conjugated chain on one side of the diarylethene. The photochromic reactivity was dependent on the arylethynyl group. Diarylethenes with m-phenylene group showed an efficient photochromic reactivity. Along with the photochromic reaction the diarylethenes showed photoswitching of an ESR spectrum originating from the change in the magnetic interaction between two unpaired electrons. The open-ring isomer showed stronger exchange interaction than the photogenerated closed-ring isomer. The magnetic interaction between two radicals via the pi-conjugated chain was altered by photocyclization due to the change of the hybrid orbital at the 2-position of the thiophene ring from sp(2) to sp(3).
• Synthesis of New Photochromic Diarylethenes Having 2,5-Bis(trimethylsilylethynyl)-3-Thienyl Unit
  作者：Naoki Tanifuji、Kenji Matsuda、Masahiro Irie

  DOI：10.1080/15421400590946190

  日期：2005.5.1

  New diarylethenes having a trimethylsilylethynyl substituent at the 2,5-position of the thiophene ring were synthesized. Diarylethene moiety are located in the middle of the pi-conjugated chain. These molecules underwent a photochromic reaction in solution. This molecule can be used as a switching unit in the it-conjugated polymer or oligomer.