pseudogem-bis(4,5-diphenyl-1H-imidazol-2-yl)[2.2]paracyclophane | 1140231-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: pseudogem-bis(4,5-diphenyl-1H-imidazol-2-yl)[2.2]paracyclophane
• 英文别名: [2.2]paracyclophane-4,13-(4,5-diphenyl-1H-imidazol-2-yl)；2-[12-(4,5-diphenyl-1H-imidazol-2-yl)-5-tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaenyl]-4,5-diphenyl-1H-imidazole
• CAS: 1140231-87-3
• 化学式: C₄₆H₃₆N₄
• 分子量: 644.819
• InChiKey: LIKKNLSDISUZSH-UHFFFAOYSA-N

物化性质

• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  50
• 可旋转键数：
  6
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pseudogem-bis(4,5-diphenyl-1H-imidazol-2-yl)[2.2]paracyclophane 在 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 苯 为溶剂， 生成 pseudogem-bisDPI[2.2]PC
  参考文献：
  名称：

  通过 1,1'-联萘桥联咪唑二聚体的短寿命咪唑基自由基产生不寻常的负光致变色

  摘要：

  我们合成了一种新的光致变色化合物，它表现出不寻常的负光致变色，其中稳定的有色物种通过短寿命自由基光化学转化为亚稳定的无色物种。该化合物具有桥连两个二苯基咪唑单元的 1,1'-联萘部分。通过纳秒激光闪光光解研究其光化学性质。有色物质在暴露于可见光后异构化为无色物质，并在室温下 20 分钟内热恢复为原始有色物质。此外，光脱色反应通过短寿命自由基进行，室温下在苯中的半衰期为 9.4 μs。

  DOI：

  10.1021/ja311344u
• 作为产物：
  描述：

  4,15-diformyl[2.2]paracyclophane 、 联苯甲酰 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以60%的产率得到pseudogem-bis(4,5-diphenyl-1H-imidazol-2-yl)[2.2]paracyclophane
  参考文献：
  名称：

  A Fast Photochromic Molecule That Colors Only under UV Light

  摘要：

  We demonstrate that photochromism based on light-driven reversible bond cleavage can enable rapid coloration upon UV light irradiation and successive fast thermal bleaching within tens of milliseconds at room temperature. We have succeeded in developing a bisimidazole derivative with a paracyclophane moiety, pseudogem-bisDP1[2.2]PC, that changes from colorless to blue when irradiated with UV light. The incident light homolytically cleaves the C-N bond that links the two imidazole rings, generating a pair of imidazotyl radicals. A paracyclophane moiety connects the two radicals, thereby preventing them from diffusing away from one another, and the radicals quickly bind with each other to flip back to the original bisimidazole. Photochromic materials showing such intense photocoloration and fast thermal bleaching performance could be promising materials for possible fast light modulator applications.

  DOI：

  10.1021/ja810032t

文献信息

• EP2397468
  申请人：——

  公开号：——

  公开（公告）日：——
• A Fast Photochromic Molecule That Colors Only under UV Light
  作者：Yuta Kishimoto、Jiro Abe

  DOI：10.1021/ja810032t

  日期：2009.4.1

  We demonstrate that photochromism based on light-driven reversible bond cleavage can enable rapid coloration upon UV light irradiation and successive fast thermal bleaching within tens of milliseconds at room temperature. We have succeeded in developing a bisimidazole derivative with a paracyclophane moiety, pseudogem-bisDP1[2.2]PC, that changes from colorless to blue when irradiated with UV light. The incident light homolytically cleaves the C-N bond that links the two imidazole rings, generating a pair of imidazotyl radicals. A paracyclophane moiety connects the two radicals, thereby preventing them from diffusing away from one another, and the radicals quickly bind with each other to flip back to the original bisimidazole. Photochromic materials showing such intense photocoloration and fast thermal bleaching performance could be promising materials for possible fast light modulator applications.
• Unusual Negative Photochromism via a Short-Lived Imidazolyl Radical of 1,1′-Binaphthyl-Bridged Imidazole Dimer
  作者：Sayaka Hatano、Takeru Horino、Atsuhiro Tokita、Toyoji Oshima、Jiro Abe

  DOI：10.1021/ja311344u

  日期：2013.2.27

  the photodecoloration reaction proceeds via a short-lived radical with a half-life of 9.4 μs in benzene at room temperature. Both the colored and colorless species show the photoinduced homolytic bond cleavage reaction of the C-N bond between the nitrogen atom of the imidazole ring and the carbon atom of the 1-position of the 1,1'-binaphthyl moiety and that of the C-C bond between each of the carbon

  我们合成了一种新的光致变色化合物，它表现出不寻常的负光致变色，其中稳定的有色物种通过短寿命自由基光化学转化为亚稳定的无色物种。该化合物具有桥连两个二苯基咪唑单元的 1,1'-联萘部分。通过纳秒激光闪光光解研究其光化学性质。有色物质在暴露于可见光后异构化为无色物质，并在室温下 20 分钟内热恢复为原始有色物质。此外，光脱色反应通过短寿命自由基进行，室温下在苯中的半衰期为 9.4 μs。