4-Dimethylamino-azobenzol-4'-aldehyd | 39208-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-Dimethylamino-azobenzol-4'-aldehyd
• 英文别名: Benzaldehyde, 4-((4-(dimethylamino)phenyl)azo)-；4-[[4-(dimethylamino)phenyl]diazenyl]benzaldehyde
• CAS: 39208-00-9
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: CVURSMYMOJMTTI-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  434.3±30.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  45
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Dimethylamino-azobenzol-4'-aldehyd 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到[4-(4-dimethylaminophenylazo)]benzaldehyde oxime
  参考文献：
  名称：

  Copper-Free “Click” Modification of DNA via Nitrile Oxide−Norbornene 1,3-Dipolar Cycloaddition

  摘要：

  Nitrile oxides react smoothly and rapidly with norbornene-modified DNA in a copper-free click reaction. The reaction allows high density functionalization of oligodeoxyribonucleotides (ODNs) with a large variety of molecules directly on solid supports and even in synthesizers without the need for an additional catalyst.

  DOI：

  10.1021/ol9005322
• 作为产物：
  描述：

  对氨基苯甲醛 、 N,N-二甲基苯胺 在 盐酸 、 sodium nitrite 、 碳酸氢钠 作用下， 以 水 为溶剂， 以76%的产率得到4-Dimethylamino-azobenzol-4'-aldehyd
  参考文献：
  名称：

  由 3-Guaiazulenyl 基团和偶氮苯单元稳定的新型单碳鎓离子化合物的制备、结构和性质：三种离域 π 电子系统的比较研究

  摘要：

  在六氟磷酸的存在下，愈创甘油醚（=7-异丙基-1,4-二甲基甘菊烯）与 4'-羟基偶氮苯-4-甲醛在甲醇中在 25 °C 下反应 2 小时，产率高达 94%。

  DOI：

  10.1246/bcsj.82.879

文献信息

• Effect of nitro substitution of azo-chalcone derivatives nano film on electrical memory properties
  作者：Quan Liu、Jiu-Fu Lu、Ling-Xia Jin

  DOI：10.1080/24701556.2020.1844236

  日期：——

  photoelectric properties. The active layer was further prepared by solution spin coating, and the morphology of the film was characterized by AFM. The electrical memory performance of the device is studied. It is found that the device has the nonvolatile binary write once read many (WORM) memory performances, and the threshold voltage of the device prepared by introducing nitro group into the molecule is

  摘要 硝基取代的偶氮查尔酮衍生物3-(4-(二甲氨基)苯基)二氮烯基)苯基)-1-(4-硝基苯基)prop-2-en-1-one( AZOC-4N )和参考化合物3-( 4-(二甲氨基)苯基)二氮烯基)苯基)-1-苯基丙-2-烯-1-酮( AZOC-H )通过克莱森施密特反应合成。采用热重法、紫外-可见光法和循环伏安法研究在共轭分子AZOC-4N中引入硝基的影响关于光电特性。通过溶液旋涂进一步制备活性层，并通过AFM表征薄膜的形貌。研究了器件的电记忆性能。发现该器件具有非易失性二进制写入一次读取多次（WORM）存储性能，分子中引入硝基制备的器件阈值电压较低—1.4 V。 最后，器件的电存储性能通过理论计算进行分析。
• New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety
  作者：D. G. Slobodinyuk、A. N. Vasyanin、I. V. Lunegov、E. V. Sklyaeva、G. G. Abashev

  DOI：10.1007/s11172-022-3417-2

  日期：2022.2

  New D-π-A-type chromophores that simultaneously incorporate N,N-dimethylaminophenyl moiety as the terminal electron-donating group and either (5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile (DCM-1) or (6-methyl-4H-pyran-4-ylidene)malononitrile (DCM-2) unit as the terminal electron-withdrawing group were synthesized. Vinylene moiety and azo group served as the π-spacer. A comparative analysis of optical and electrochemical properties of the synthesized chromophores revealed that the replacement of the DCM-1 unit with the DCM-2 moiety led to chromophore band gap broadening and a decrease in the molar extinction coefficient value; while the replacement of the DCM-1 unit with the DCM-2 one in the chromophores bearing the vinylene π-spacers led to a sharp increase in the fluorescence quantum yield.

  我们合成了新的 D-π-A 型发色团，这些发色团同时包含 N,N-二甲基氨基苯基作为末端电子供体，以及 (5,5 二甲基环己-2-烯-1-亚基)丙二腈 (DCM-1) 或 (6-甲基-4H-吡喃-4-亚基)丙二腈 (DCM-2) 单元作为末端电子吸收基团。乙烯基和偶氮基团作为π-间隔物。对所合成发色团的光学和电化学性质进行的比较分析表明，用 DCM-2 基团取代 DCM-1 单元会导致发色团带隙变宽，摩尔消光系数值降低；而在带有乙烯基 π-垫片的发色团中，用 DCM-2 取代 DCM-1 单元会导致荧光量子产率急剧增加。
• Azobenzene‐Based Colorimetric Chemosensors for Rapid Naked‐Eye Detection of Mercury(II)
  作者：Xiaohong Cheng、Qianqian Li、Conggang Li、Jingui Qin、Zhen Li

  DOI：10.1002/chem.201003275

  日期：2011.6.20

  Two new highly selective colorimetric chemosensors for Hg2+, based on azobenzene and highly selective Hg2+‐promoted deprotection of a dithioacetal have been designed and synthesized. In the presence of as little as 20 μM Hg2+, the sensors change their color from light yellow to deep red, which can easily be observed by the naked eye. The underlying signaling mechanism is intramolecular charge transfer

  两个新的高选择性比色化学传感器对Hg 2+，基于偶氮苯和高选择性汞2+一个二硫的促进的去保护已设计并合成。在存在低至20μM Hg 2+的情况下，传感器的颜色从浅黄色变为深红色，可以用肉眼轻松观察到。潜在的信号传导机制是分子内电荷转移（ICT）。传感器对Hg 2+相对于几种常见的碱金属，碱土金属和过渡金属离子具有良好的选择性。此外，它们可以通过量油尺方法用于现场测量，而无需任何其他设备。
• Perez-Moreno, Javier; Zhao, Yuxia; Clays, Koen, Journal of the American Chemical Society, 2009, vol. 131, p. 5084 - 5093
  作者：Perez-Moreno, Javier、Zhao, Yuxia、Clays, Koen、Kuzyk, Mark G.、Shen, Yuquan、et al.

  DOI：——

  日期：——
• Fluorescence Quenchers for Hydrazone and Oxime Orthogonal Bioconjugation
  作者：Pete Crisalli、Armando R. Hernández、Eric T. Kool

  DOI：10.1021/bc300344b

  日期：2012.9.19

  We describe the synthesis and properties of new fluorescence quenchers containing aldehyde, hydrazine, and aminooxy groups, allowing convenient bioconjugation as oximes or hydrazones. Conjugation to oligonucleotides proceeded in high yield with aniline as catalyst. Kinetics studies of conjugation show that, under optimal conditions, a hydrazine or aminooxy quencher can react with aldehyde-modified DNA to form a stable hydrazone or oxime adduct in as little as five minutes. The resulting quencher-containing DNAs were assessed for their ability to quench the emission of fluorescein in labeled complements and compared to the commercially available dabcyl and Black Hole Quencher 2 (BHQ2), which were conjugated as phosphoramidites. Results show that the new quenchers possess slightly different absorbance properties compared to dabcyl and are as efficient as the commercial quenchers in quenching fluorescein emission. Hydrazone-based quenchers were further successfully incorporated into molecular beacons and shown to give high signal to background ratios in single nucleotide polymorphism detection in vitro. Finally, aminooxy and hydrazine quenchers were applied to quenching of an aldehyde-containing fluorophore associated with living cells, demonstrating cellular quenching within one hour.

表征谱图