4-[[4-(dibutylamino)phenyl]diazenyl]benzaldehyde | 919111-85-6

• 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-[[4-(dibutylamino)phenyl]diazenyl]benzaldehyde
• 英文别名: 4-[4-(dibutylamino)phenylazo]benzaldehyde；4-(4-dibutylaminophenylazo)benzaldehyde；p-dibutylaminophenylazobenzaldehyde
• CAS: 919111-85-6
• 化学式: C₂₁H₂₇N₃O
• 分子量: 337.465
• InChiKey: VDJCPNQKHVIFMD-GHVJWSGMSA-N

物化性质

• 沸点：
  500.1±35.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.03
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2’-联吡啶-4,4’-二甲磷酸二乙酯 、 4-[[4-(dibutylamino)phenyl]diazenyl]benzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到4,4'-bis{[p-(N,N-dibutylamino)phenylazo]styryl}-2,2'-bipyridine
  参考文献：
  名称：

  All-Optical Orientation of Photoisomerizable Octupolar Zinc(II) Complexes in Polymer Films

  摘要：

  A new type of 4,4'-bis(styryl)-2,2'-bipyridine functionalized by a dialkylamino-azobenzene group has been prepared. This ligand has allowed the preparation of photoisomerizable octupolar tris(bipyridyl)zinc(II) complexes and the corresponding star-shaped polymer by atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA). The photoisomerization properties of such new metallo-chromophores have been studied. The macroscopic molecular orientation of the corresponding doped and grafted NLO-polymer films is reported for the first time.

  DOI：

  10.1021/ja048143z
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 [4-(4-bromophenylazo)phenyl]dibutylamine 在 正丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 4.25h， 以78%的产率得到4-[[4-(dibutylamino)phenyl]diazenyl]benzaldehyde
  参考文献：
  名称：

  Lemercier; Alexandre; Mulatier, Journal of Chemical Research, Synopses, 2003, # 9, p. 542 - 543

  摘要：

  DOI：

文献信息

• Analogs of Michler’s ketone for two-photon absorption initiation of polymerization in the near infrared: synthesis and photophysical properties
  作者：Gilles Lemercier、Cécile Martineau、Jean-Christophe Mulatier、Irène Wang、Olivier Stéphan、Patrice Baldeck、Chantal Andraud

  DOI：10.1039/b608391a

  日期：——

  We present the synthesis of substituted ketones, conjugated analogs of Michler’s ketone. These molecules exhibit broadband TPA properties between 700 and 1100 nm due to a charge transfer from the terminal amino groups to the central ketone function and with maximum cross sections from 200 to 325 × 10−50 cm4 s photon−1. Moreover, they present an interesting reducing character for radical creation. Both properties allow us to consider these molecules as promising photoinitiators of polymerization in the near infrared.

  我们合成了取代酮--Michler酮的共轭类似物。由于电荷从末端氨基转移到中心酮功能，这些分子在 700 至 1100 纳米波长范围内表现出宽带 TPA 特性，最大截面为 200 至 325 Ã 10â50 cm4 s 光子1。此外，它们还能产生有趣的还原性自由基。这两种特性使我们能够将这些分子视为有前景的近红外聚合光引发剂。
• Optical article containing a polymer that exhibits nonlinear second order polarization susceptibility
  申请人：EASTMAN KODAK COMPANY

  公开号：EP0654696A1

  公开（公告）日：1995-05-24

  An optical article exhibits effects attributable to the nonlinear second order polarizability of electromagnetic radiation and comprises a polymer containing within its repeating units polar aligned noncentrosymmetric molecular dipoles having an electron donor moiety linked through a conjugated π bonding system to an electron acceptor moiety to permit oscillation of the molecular dipoles between a ground state exhibiting a first dipole moment and an excited state exhibiting a different dipole moment, characterized in that the molecular dipoles include as an acceptor moiety a vinyl group geminally substituted by two strong electron withdrawing groups, at least one of which is a perfluoroalkylsulfonyl moiety.

  一种光学制品具有可归因于电磁辐射非线性二阶极化性的效应，它包括一种聚合物，在其重复单元中含有极性排列的非中心对称分子偶极子，该分子偶极子具有一个电子供体分子，通过共轭π键系统与一个电子受体分子相连接，使分子偶极子在显示第一偶极矩的基态和显示不同偶极矩的激发态之间振荡、其特征在于，分子偶极子包括作为受体分子的乙烯基，该乙烯基被两个强取电子基团取代，其中至少一个是全氟烷基磺酰基。
• New bichromophoric-2,2′-bipyridines: synthesis and optical properties
  作者：Olivier Lohio、Lydie Viau、Olivier Maury、Hubert Le Bozec

  DOI：10.1016/j.tetlet.2006.12.048

  日期：2007.2

  The synthesis and characterization of new unsymmetrically substituted bipyridyl-based chromophores featuring pi-conjugated donor, acceptor or photoisomerizable backbones are reported. Their absorption and emission proporties are discussed ill comparison to those of the parent ligands. (c) 2006 Elsevier Ltd. All rights reserved.
• US5381507A
  申请人：——

  公开号：US5381507A

  公开（公告）日：1995-01-10
• All-Optical Orientation of Photoisomerizable Octupolar Zinc(II) Complexes in Polymer Films
  作者：Lydie Viau、Sébastien Bidault、Olivier Maury、Sophie Brasselet、Isabelle Ledoux、Joseph Zyss、Eléna Ishow、Keitaro Nakatani、Hubert Le Bozec

  DOI：10.1021/ja048143z

  日期：2004.7.14

  A new type of 4,4'-bis(styryl)-2,2'-bipyridine functionalized by a dialkylamino-azobenzene group has been prepared. This ligand has allowed the preparation of photoisomerizable octupolar tris(bipyridyl)zinc(II) complexes and the corresponding star-shaped polymer by atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA). The photoisomerization properties of such new metallo-chromophores have been studied. The macroscopic molecular orientation of the corresponding doped and grafted NLO-polymer films is reported for the first time.