(E)-N-(anthracene-9-yl-methylene)benzohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (E)-N-(anthracene-9-yl-methylene)benzohydrazide
• 英文别名: (E)-N'-(anthracen-9-ylmethylene)benzhydrazide；N'-[(E)-anthracen-9-ylmethylidene]benzohydrazide；N-[(E)-anthracen-9-ylmethylideneamino]benzamide
• 化学式: C₂₂H₁₆N₂O
• 分子量: 324.382
• InChiKey: QUYNMUOXPCAKME-HZHRSRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-(anthracene-9-yl-methylene)benzohydrazide 以 乙腈 为溶剂， 反应 0.33h， 生成 (Z)-N'-(anthracen-9-ylmethylene)benzhydrazide
  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：

  (Z)-N'-(anthracen-9-ylmethylene)benzhydrazide 以 乙腈 为溶剂， 反应 0.42h， 生成 (E)-N-(anthracene-9-yl-methylene)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

文献信息

• Co(III) and Ni(II) complexes of an anthracene appended aroyl hydrazone: Synthesis, crystal structures, DNA binding and catecholase activity
  作者：Satyajit Mondal、Bholanath Pakhira、Alexander J. Blake、Mike G.B. Drew、Shyamal Kumar Chattopadhyay

  DOI：10.1016/j.poly.2016.05.052

  日期：2016.10

  Abstract The Co(III) and Ni(II) complexes [Co(L2)2(bpy)]Cl (1) and [Ni(L2)2(phen)] (2) (where L2 is a monoanionic bidentate hydrazone ligand and bpy = 2,2′-bipyridine, phen = 1,10-phenanthroline) have been synthesized and characterized by infra-red, UV–Vis, ESI-MS spectroscopies and elemental analyses. Complexes 1 and 2 were structurally characterized by single crystal X-ray diffraction. Structural analysis

  摘要Co（III）和Ni（II）配合物[Co（L2）2（bpy）] Cl（1）和[Ni（L2）2（phen）]（2）（其中L2是单阴离子双齿配体，已经合成了bpy = 2,2'-联吡啶，phen = 1,10-菲咯啉，并通过红外，UV-Vis，ESI-MS光谱学和元素分析对其进行了表征。配合物1和2通过单晶X射线衍射在结构上表征。结构分析显示，金属中心周围的八面体配体扭曲，带有MN4O2发色团[M = Co（III）和Ni（II）]，配体充当单阴离子双齿N，O-给体。配合物1和2与小牛胸腺DNA（CT-DNA）的结合通过UV-Vis吸收，荧光光谱和粘度测量进行了研究。复合物1具有3,5-二叔丁基邻苯二酚（3,5-二叔丁基邻苯二酚 5-DTBCH2）作为底物。动力学测量表明，相对于底物，邻苯二酚的氧化速率遵循饱和动力学，并且发现kcat值非常高，值为1.00×105 h-1。
• Azoanthracene-core structure as Cu2+-assisted CO sensing probe: Characterization, performance, and bioimaging
  作者：Tiantian Lin、Lina Song、Chunguo Cui、Xiao Kong、Kaiyao Shi

  DOI：10.1016/j.saa.2024.124122

  日期：2024.5

  signal transduction and therapeutic effects in vital biological activities. Fluorescence imaging has proven a powerful tool for detecting endogenous CO, which drives the development of low-cost and easy-to-use fluorescent probes. In this study, four azobenzene derivatives (A1, A2, A3, and A4) with various substituents were reported, including their geometric structures, photophysical parameters, and spectral

  内源性 CO（一氧化碳）的检测是生物学中一个有趣的话题，因为它被发现是重要生物活动中信号转导和治疗作用的信使。荧光成像已被证明是检测内源 CO 的强大工具，这推动了低成本且易于使用的荧光探针的开发。在本研究中，报道了四种具有不同取代基的偶氮苯衍生物（A1、A2、A3和A4），包括它们的几何结构、光物理参数以及对Cu和CO的光谱响应。讨论了取代基结构与性能之间的关系Cu 淬灭和 CO 传感机制。最佳探针（A1）没有取代基，在Cu存在下能有效猝灭荧光，其PLQY从0.33下降到0.02，PLQY=光致发光量子产率。 CO脱氧后，A1的荧光可在180 s内恢复（PLQY恢复至0.32）。其传感机制是静态的，通过与 Cu 形成非荧光络合物（化学计量比为 1:1）。报道了 A1 对 HeLa 细胞内源性 CO 的生物成像性能。
• VISUAL DETECTION OF FLUORIDE IONS
  申请人：INDIAN INSTITUTE OF TECHNOLOGY MADRAS

  公开号：US20140357894A1

  公开（公告）日：2014-12-04

  Dendrimer-hydrazides are coupled to polycyclic aromatic hydrocarbons for use in the visual detection of the presence of low levels of fluoride in a sample. The dendrimers can have a phenyl core, a first generation of aralkyl ethers, and an optional second generation of aralkyl ethers. The compounds form gels with solvents. In the presence of fluoride ion, the gels undergo color changes and/or gel to liquid phase change.
• US8828735B2
  申请人：——

  公开号：US8828735B2

  公开（公告）日：2014-09-09
• US9201001B2
  申请人：——

  公开号：US9201001B2

  公开（公告）日：2015-12-01