1,2-bis[6-(1-oxyl-3-oxide-4,4,5,5-tetramethylimidazolin-2-yl)-2-methylbenzo[b]-thiophen-3-yl]hexafluorocyclopentene | 258834-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,2-bis[6-(1-oxyl-3-oxide-4,4,5,5-tetramethylimidazolin-2-yl)-2-methylbenzo[b]-thiophen-3-yl]hexafluorocyclopentene
• CAS: 258834-25-2
• 化学式: C₃₇H₃₆F₆N₄O₄S₂
• 分子量: 778.84
• InChiKey: VTPQXWNTILXKAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.51
• 重原子数：
  53.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  98.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2-bis[6-(1-oxyl-3-oxide-4,4,5,5-tetramethylimidazolin-2-yl)-2-methylbenzo[b]-thiophen-3-yl]hexafluorocyclopentene 以 乙酸乙酯 为溶剂， 生成 2-[(1R,2R)-12,12,13,13,14,14-hexafluoro-1,2-dimethyl-20-(4,4,5,5-tetramethyl-1,3-dioxidoimidazolidin-2-ylidene)-3,23-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4,7,9,11(15),16,18,21-heptaen-6-ylidene]-4,4,5,5-tetramethylimidazolidine-1,3-diium 1,3-dioxide
  参考文献：
  名称：

  A Diarylethene with Two Nitronyl Nitroxides:  Photoswitching of Intramolecular Magnetic Interaction

  摘要：

  A diarylethene having two nitronyl nitroxides, 1,2-bis[6-(1-oxyl-3-oxide-4,3,5,5-tetramethylimidazolin-2-yl) -2-methyl-1-benzothiophen-3-yl]hexafluorocyclopentene (2a), was synthesized in an attempt to control the intramolecular magnetic interaction by photoirradiation. The photochemical conversions from open-ring isomer 2a to closed-ring isomer 2b and from 2b to 2a were both almost 100%. Magnetic measurement revealed the antiferromagnetic interaction between two nitronyl nitroxides remarkably increased from 2J/k(B) = -2.2 K to 2J/k(B) = -11.6 K when the diarylethene spin coupler was switched from the open-ring isomer 2a to the closed-ring isomer 2b. ESR measurements were also carried out for both 2a and 2b in benzene solutions at room temperature and in MTHF solid solutions at cryogenic temperature. Both ESR and magnetic measurement indicated that the intramolecular interaction was switched by the photochromic spin coupler.

  DOI：

  10.1021/ja000605v
• 作为产物：
  描述：

  1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯 在 三氯化铝 、 potassium carbonate 作用下， 以 甲醇 、 硝基苯 为溶剂， 反应 40.0h， 生成 1,2-bis[6-(1-oxyl-3-oxide-4,4,5,5-tetramethylimidazolin-2-yl)-2-methylbenzo[b]-thiophen-3-yl]hexafluorocyclopentene
  参考文献：
  名称：

  A Diarylethene with Two Nitronyl Nitroxides:  Photoswitching of Intramolecular Magnetic Interaction

  摘要：

  A diarylethene having two nitronyl nitroxides, 1,2-bis[6-(1-oxyl-3-oxide-4,3,5,5-tetramethylimidazolin-2-yl) -2-methyl-1-benzothiophen-3-yl]hexafluorocyclopentene (2a), was synthesized in an attempt to control the intramolecular magnetic interaction by photoirradiation. The photochemical conversions from open-ring isomer 2a to closed-ring isomer 2b and from 2b to 2a were both almost 100%. Magnetic measurement revealed the antiferromagnetic interaction between two nitronyl nitroxides remarkably increased from 2J/k(B) = -2.2 K to 2J/k(B) = -11.6 K when the diarylethene spin coupler was switched from the open-ring isomer 2a to the closed-ring isomer 2b. ESR measurements were also carried out for both 2a and 2b in benzene solutions at room temperature and in MTHF solid solutions at cryogenic temperature. Both ESR and magnetic measurement indicated that the intramolecular interaction was switched by the photochromic spin coupler.

  DOI：

  10.1021/ja000605v

文献信息

• Effect of Imino Nitroxyl and Nitronyl Nitroxyl Groups on the Photochromic Reactivity of Diarylethenes
  作者：Naoki Tanifuji、Kenji Matsuda、Masahiro Irie

  DOI：10.1021/ol051463i

  日期：2005.8.1

  Diarylethene derivatives having imino nitroxide and nitronyl nitroxide have been prepared to examine the effect of the radical substituents on the photochromic reactivity of 1,2-bis(2-methyl-1-benzothiophen-3-yl)perfluorocyclopentene. These radical substituents reduce the quantum yields of both cyclization and cycloreversion reactions. The nitronyl nitroxyl moiety is more effective to suppress the reactivity in comparison with the imino nitroxide moiety.
• Photochromism of diarylethenes having nitronyl nitroxides
  作者：Kenji Matsuda、Masahiro Irie

  DOI：10.1016/s0040-4039(00)00209-4

  日期：2000.4

  The photoreactivities of photochromic diarylethenes having nitronyl nitroxide radicals were studied in terms of the measurement of the quantum yields and the conversions in the photostationary state. (C) 2000 Elsevier Science Ltd. All rights reserved.