(Z)-N'-(thiophen-2-ylmethylene)benzhydrazide

• 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: (Z)-N'-(thiophen-2-ylmethylene)benzhydrazide
• 英文别名: N-[(Z)-thiophen-2-ylmethylideneamino]benzamide
• 化学式: C₁₂H₁₀N₂OS
• 分子量: 230.29
• InChiKey: CSNLKZXFSZSMCJ-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N'-(thiophen-2-ylmethylene)benzhydrazide 以 乙腈 为溶剂， 反应 2.0h， 生成 (E)-N'-(thiophen-2-ylmethylene)benzohydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  (E)-N'-(thiophen-2-ylmethylene)benzohydrazide 生成 (Z)-N'-(thiophen-2-ylmethylene)benzhydrazide
  参考文献：
  名称：

  有机化合物及其制备方法、显示基板和显示装置

  摘要：

  公开一种有机化合物及其制备方法、显示基板和显示装置，涉及显示技术领域，用于提高显示装置的显示效果与使用寿命。该有机化合物的结构式如下式(I)所示：

  公开号：

  CN114369059A

文献信息

• Photochemistry of arylhydrazides in solution
  作者：D. G. Belov、B. G. Rogachev、L. I. Tkachenko、V. A. Smirnov、S. M. Aldoshin

  DOI：10.1007/bf02495478

  日期：2000.4

  The photochemical reactions of arylhydrazides ArCONHN=CHR in solution were studied. The main photochemical process was shown to be trans-cis isomerization with a quantum yield of 0.2-0.8 and an activation energy of 21-24 kcal mol(-1).