1-trityl-4-phenylazoimidazole | 1367346-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-trityl-4-phenylazoimidazole
• CAS: 1367346-18-6
• 化学式: C₂₈H₂₂N₄
• 分子量: 414.509
• InChiKey: VMHWFZGJZSARBL-NVQSTNCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  42.54
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-trityl-4-phenylazoimidazole 生成 1-trityl-4-phenylazoimidazole
  参考文献：
  名称：

  Photoswitchable Azoheterocycles via Coupling of Lithiated Imidazoles with Benzenediazonium Salts

  摘要：

  In contrast to azobenzenes, heterocyclic azo compounds are less well investigated. Phenylazoimidazoles would be versatile as photodissociable ligands (PDLs) because imidazole is an important donor in coordination chemistry. Here, we present the synthesis of 4- and 5-phenylazoimidazoles via a novel azo-coupling method. 1,2-Protected imidazole is lithiated in the 5-position and coupled with benzenediazonium tetrafluoroborate. Several new phenylazoimidazoles were prepared. They exhibit an excellent switching behavior. Upon irradiation of the trans isomers with UV light, >95% of the cis forms are obtained. Upon heating, a complete transformation back to the trans configuration was achieved. Back switching with visible light, however, is incomplete.

  DOI：

  10.1021/jo202688x
• 作为产物：
  描述：

  在 盐酸 、 四丁基氟化铵 、 水 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 acetontrile 、 乙醇 为溶剂， 反应 8.0h， 生成 1-trityl-4-phenylazoimidazole
  参考文献：
  名称：

  Photoswitchable Azoheterocycles via Coupling of Lithiated Imidazoles with Benzenediazonium Salts

  摘要：

  In contrast to azobenzenes, heterocyclic azo compounds are less well investigated. Phenylazoimidazoles would be versatile as photodissociable ligands (PDLs) because imidazole is an important donor in coordination chemistry. Here, we present the synthesis of 4- and 5-phenylazoimidazoles via a novel azo-coupling method. 1,2-Protected imidazole is lithiated in the 5-position and coupled with benzenediazonium tetrafluoroborate. Several new phenylazoimidazoles were prepared. They exhibit an excellent switching behavior. Upon irradiation of the trans isomers with UV light, >95% of the cis forms are obtained. Upon heating, a complete transformation back to the trans configuration was achieved. Back switching with visible light, however, is incomplete.

  DOI：

  10.1021/jo202688x

文献信息

• Tuning Azoheteroarene Photoswitch Performance through Heteroaryl Design
  作者：Joaquín Calbo、Claire E. Weston、Andrew J. P. White、Henry S. Rzepa、Julia Contreras-García、Matthew J. Fuchter

  DOI：10.1021/jacs.6b11626

  日期：2017.1.25

  switching and long Z isomer half-life). Here we present a systematic computational and experimental study to elucidate the origin of the long thermal half-lives and excellent addressability of the arylazopyrazoles, and apply this understanding to determine important structure-property relationships for a wide array of comparable azoheteroaryl photoswitches. We identify compounds with Z isomer half-lives ranging

  光可切换化合物可以通过光在两种异构体之间可逆地切换，继续引起广泛应用的显着关注。偶氮杂芳烃代表了一种相对较新但研究不足的光开关类型，其中传统偶氮苯类中的一个芳环已被五元杂芳环取代。初步研究表明，偶氮杂芳烃——特别是芳基并吡唑——具有优异的光开关特性（定量开关和长 Z 异构体半衰期）。在这里，我们提出了一项系统的计算和实验研究，以阐明芳基并吡唑的长热半衰期和优异的可寻址性的起源，并应用这一理解来确定各种可比较的偶氮杂芳基光开关的重要结构-性质关系。我们通过杂环的调节，鉴定了具有 Z 异构体半衰期从几秒到几小时、到几天甚至几年以及可变吸收特性的化合物。构象可能在决定这些性质方面发挥着最大的作用：异构化半衰期最长的化合物采用 T 形基态 Z 异构体构象并通过 T 形异构化途径进行，而对于具有最长异构化半衰期的化合物，实现了最完整的光开关具有扭曲（而不是 T 形）的 Z 异构体构象。通过平衡这些因素，我们报告了一种新的偶氮吡唑