| 1075707-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1075707-14-0
• 化学式: C₃₁H₂₇N₄S₂*I
• 分子量: 646.619
• InChiKey: BSTKCBQOWINVBN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  38.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  33.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  生成 1,3-dimethyl-4,5-bis(5-methyl-2-phenylthiazol-4-yl)-2-phenyl-1H-imidazolium iodide
  参考文献：
  名称：

  Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium

  摘要：

  An interconversion system between imidazolium and imidazolinium has been proposed for the first time. Imidazolium and imidazolinium cations exhibit different reactivity due to the difference in the aromaticity and charge localization structure, which is successfully controlled by means of photoirradiation in the present system. A 4,5-dithiazolylimidazolium salt was prepared and studied as a new class of photochromic materials modulating electrostatic interactions and chemical reactivities. The photochromic 4,5-dithiazolylimidazolium showed reversible photoconversions between imidazolium open-form and imidazolinium closed-form upon successive irradiation with UV and visible light. The imidazolinium closed-form exhibited characteristic solvato- and ionochromisms in which the absorption maximum shifted by more than 80 nm depending on the solvent polarity and counteranions, whereas the imidazolium open-form showed no such solvent-dependent property. Because the corresponding nonionic 4,5-dithiazolylimidazole also did not exhibit the solvent-dependent absorption profile both in open- and closed-forms, the appearance of these chromisms in imidazolinium closed-form was attributed to the change in the extent of ionic interaction, which was brought about by the photoconversion of imidazolium to imidazolinium. The photoderived strong ionic interaction of imidazolinium with counteranion was further applied to the photocontrolled nucleophilic reaction system. Whereas the imidazolium open-form was inert to nucleophiles such as sodium methoxide, the imidazolinium closed-form was reactive to the nucleophilic reaction, demonstrating a photogated reaction system.

  DOI：

  10.1021/ja802986y
• 作为产物：
  描述：

  1,3-dimethyl-4,5-bis(5-methyl-2-phenylthiazol-4-yl)-2-phenyl-1H-imidazolium iodide 生成
  参考文献：
  名称：

  Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium

  摘要：

  An interconversion system between imidazolium and imidazolinium has been proposed for the first time. Imidazolium and imidazolinium cations exhibit different reactivity due to the difference in the aromaticity and charge localization structure, which is successfully controlled by means of photoirradiation in the present system. A 4,5-dithiazolylimidazolium salt was prepared and studied as a new class of photochromic materials modulating electrostatic interactions and chemical reactivities. The photochromic 4,5-dithiazolylimidazolium showed reversible photoconversions between imidazolium open-form and imidazolinium closed-form upon successive irradiation with UV and visible light. The imidazolinium closed-form exhibited characteristic solvato- and ionochromisms in which the absorption maximum shifted by more than 80 nm depending on the solvent polarity and counteranions, whereas the imidazolium open-form showed no such solvent-dependent property. Because the corresponding nonionic 4,5-dithiazolylimidazole also did not exhibit the solvent-dependent absorption profile both in open- and closed-forms, the appearance of these chromisms in imidazolinium closed-form was attributed to the change in the extent of ionic interaction, which was brought about by the photoconversion of imidazolium to imidazolinium. The photoderived strong ionic interaction of imidazolinium with counteranion was further applied to the photocontrolled nucleophilic reaction system. Whereas the imidazolium open-form was inert to nucleophiles such as sodium methoxide, the imidazolinium closed-form was reactive to the nucleophilic reaction, demonstrating a photogated reaction system.

  DOI：

  10.1021/ja802986y