(Z)-N'-(anthracen-9-ylmethylene)isonicotinic hydrazide | 1305101-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (Z)-N'-(anthracen-9-ylmethylene)isonicotinic hydrazide
• 英文别名: N-[(Z)-anthracen-9-ylmethylideneamino]pyridine-4-carboxamide
• CAS: 1305101-18-1
• 化学式: C₂₁H₁₅N₃O
• 分子量: 325.37
• InChiKey: SFZNDNWHTDVIPK-UCQKPKSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N'-(anthracen-9-ylmethylene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.53h， 生成 (E)-N'-(anthracen-9-ylmethylene)isonicotinic hydrazide
  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'-(anthracen-9-ylmethylene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.25h， 生成 (Z)-N'-(anthracen-9-ylmethylene)isonicotinic hydrazide
  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

文献信息

• A colorimetric and fluorescent chemosensor for the detection of an explosive—2,4,6-trinitrophenol (TNP)
  作者：Yu Peng、Ai-Jiang Zhang、Ming Dong、Ya-Wen Wang

  DOI：10.1039/c1cc10400d

  日期：——

  A fluorescent and colorimetric receptor (L) for specific recognition of TNP was described. The origins of this remarkable affinity was disclosed by the crystal structure of corresponding host–guest complex L·TNP.

  描述了一种用于特异性识别 TNP 的荧光和比色受体 (L)。这种显着亲和力的起源由相应的主客体复合物L·TNP的晶体结构揭示。