4-cyano-4′-(12″-bromododecyloxy)azobenzene | 296248-02-7

• 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-cyano-4′-(12″-bromododecyloxy)azobenzene
• 英文别名: 1-bromo-12-(4-((4-cyanophenyl)diazenyl)phenoxy)dodecane；4-cyano-4'-(12"-bromododecyloxy)azobenzene；4-[[4-(12-Bromododecoxy)phenyl]diazenyl]benzonitrile；4-[[4-(12-bromododecoxy)phenyl]diazenyl]benzonitrile
• CAS: 296248-02-7
• 化学式: C₂₅H₃₂BrN₃O
• 分子量: 470.453
• InChiKey: YMJLPEOPJOGFJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  没食子酸甲酯 、 4-cyano-4′-(12″-bromododecyloxy)azobenzene 在 potassium carbonate 、 potassium iodide 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以54%的产率得到methyl 3,4,5-tris[12-(4-(4′-cyanophenyldiazo)phenoxy)dodecyloxy]benzoate
  参考文献：
  名称：

  Self-Assembly and Photoinduced Optical Anisotropy in Dendronized Supramolecular Azopolymers

  摘要：

  Herein we report the preparation and characterization of dendronized supramolecular polymers composed of a carboxy-terminated azodendron, dAZO, and two different vinylpyridine-containing polymers: poly(4-vinylpyridine) (P4VP) and polystyrene-b-poly(4-vinylpyridine) (PS-b-P4VP) block copolymer. P4VP can selectively complex dAZO through hydrogen-bonding interactions, thus resulting in liquid crystalline materials. Additionally, this strategy is also applicable to the preparation of dendronized supramolecular block copolymers (BCs). Lamellar, cylindrical, and spherical morphologies are observed for the BC complexes depending on the dAZO to vinylpyridine repeating unit ratio. Photoinduced orientation of the azobenzene moieties is obtained in films of the H-bonded materials-both P4VP and PS-b-P4VP based complexes-by using 488 nm linearly polarized light and characterized through birefringence and dichroism measurements. High and, stable values of birefringence are obtained for polymers with azobenzene content as low as 2.7 wt %, thus demonstrating the benefits of preorganization in photoactive dendritic moieties in side-chain H-bonded materials.

  DOI：

  10.1021/ma402369p
• 作为产物：
  描述：

  1,12-二溴十二烷 、 4-[4-(cyanophenyl)azo]phenol 在 18-冠醚-6 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以67%的产率得到4-cyano-4′-(12″-bromododecyloxy)azobenzene
  参考文献：
  名称：

  光敏聚合物和嵌段共聚物通过基于多个氢键的分子识别

  摘要：

  合成了一种新的含2,6-二酰基氨基吡啶（DAP）基团的甲基丙烯酸酯，并通过RAFT聚合进行了聚合，以制备均聚甲基丙烯酸酯（PDAP）和与聚甲基丙烯酸甲酯嵌段（PMMA- b‐PDAP）。这些聚合物可以容易地与具有胸腺嘧啶（tAZO）或具有树突结构的羧基（dAZO）的偶氮苯生色团络合，后者可以分别与DAP基团形成三个或两个氢键。超分子聚合物通过光谱技术，光学显微镜，TGA和DSC进行表征。具有dAZO的超分子聚合物和嵌段共聚物表现出介晶性能，而具有tAZO的超分子聚合物和嵌段共聚物是非晶态材料。还研究了超分子聚合物对线偏振光照射的响应，发现尽管在包含树枝状发色团dAZO的聚合物中获得了更高的双折射和二向色性值，但在所有材料中均可以光诱导出稳定的光学各向异性。©2014 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学2014，52，3173-3184

  DOI：

  10.1002/pola.27373

文献信息

• Photoresponsive polymers and block copolymers by molecular recognition based on multiple hydrogen bonds
  作者：Alberto Concellón、Eva Blasco、Milagros Piñol、Luis Oriol、Isabel Díez、Cristina Berges、Carlos Sánchez-Somolinos、Rafael Alcalá

  DOI：10.1002/pola.27373

  日期：2014.11.15

  group was synthesized and polymerized via RAFT polymerization to prepare homopolymethacrylates (PDAP) and diblock copolymers combined with a poly(methyl methacrylate) block (PMMA‐b‐PDAP). These polymers can be easily complexed with azobenzene chromophores having thymine (tAZO) or carboxylic groups with a dendritic structure (dAZO), which can form either three or two hydrogen bonds with the DAP groups, respectively

  合成了一种新的含2,6-二酰基氨基吡啶（DAP）基团的甲基丙烯酸酯，并通过RAFT聚合进行了聚合，以制备均聚甲基丙烯酸酯（PDAP）和与聚甲基丙烯酸甲酯嵌段（PMMA- b‐PDAP）。这些聚合物可以容易地与具有胸腺嘧啶（tAZO）或具有树突结构的羧基（dAZO）的偶氮苯生色团络合，后者可以分别与DAP基团形成三个或两个氢键。超分子聚合物通过光谱技术，光学显微镜，TGA和DSC进行表征。具有dAZO的超分子聚合物和嵌段共聚物表现出介晶性能，而具有tAZO的超分子聚合物和嵌段共聚物是非晶态材料。还研究了超分子聚合物对线偏振光照射的响应，发现尽管在包含树枝状发色团dAZO的聚合物中获得了更高的双折射和二向色性值，但在所有材料中均可以光诱导出稳定的光学各向异性。©2014 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学2014，52，3173-3184
• Synthesis, characterization, and photoresponsive behavior of a series of azobenzene-containing side-chain poly(ether sulfone)s with various lengths of flexible spacers
  作者：Yuxuan Zhang、Songhao Pei、Yongpeng Wang、Zengduo Cui、Na Li、Ye Zhu、Haibo Zhang、Zhenhua Jiang

  DOI：10.1016/j.dyepig.2013.08.004

  日期：2013.12

  A series of azobenzene-containing side-chain poly(ether sulfone)s (azo-PES) with various spacer lengths (2, 6 or 12 methylene units) were successfully synthesized via a nucleophilic substitution grafting reaction between poly(ether sulfone)s with hydroxylphenyl side groups and azobenzene monomers. Their chemical structures and properties were characterized by means of IR, UV–vis and 1H NMR. These azo-polymers

  通过聚（醚砜）与聚（醚砜）之间的亲核取代接枝反应成功地合成了一系列具有不同间隔长度（2个，6个或12个亚甲基单元）的含偶氮侧链聚（醚砜）（偶氮PES）。羟苯基侧基和偶氮苯单体。通过IR，UV-vis和1对它们的化学结构和性质进行了表征。1 H NMR。这些偶氮聚合物在玻璃化转变温度和119°C和347°C以上的5％失重温度下表现出良好的热稳定性。光异构化实验的结果表明，具有更长间隔基的偶氮-PES聚合物对应于更高的光异构化速率。在用532 nm掺钕钇铝石榴石（Nd：YAG）激光束照射时，它们呈现出的双折射残余值大于双折射饱和值的82％，表明光诱导取向的良好稳定性。在几次刻写-擦除-刻写序列循环之后，未观察到疲劳现象。
• Self-Assembly and Photoinduced Optical Anisotropy in Dendronized Supramolecular Azopolymers
  作者：Jesús del Barrio、Eva Blasco、Chris Toprakcioglu、Alexandros Koutsioubas、Oren A. Scherman、Luis Oriol、Carlos Sánchez-Somolinos

  DOI：10.1021/ma402369p

  日期：2014.2.11

  Herein we report the preparation and characterization of dendronized supramolecular polymers composed of a carboxy-terminated azodendron, dAZO, and two different vinylpyridine-containing polymers: poly(4-vinylpyridine) (P4VP) and polystyrene-b-poly(4-vinylpyridine) (PS-b-P4VP) block copolymer. P4VP can selectively complex dAZO through hydrogen-bonding interactions, thus resulting in liquid crystalline materials. Additionally, this strategy is also applicable to the preparation of dendronized supramolecular block copolymers (BCs). Lamellar, cylindrical, and spherical morphologies are observed for the BC complexes depending on the dAZO to vinylpyridine repeating unit ratio. Photoinduced orientation of the azobenzene moieties is obtained in films of the H-bonded materials-both P4VP and PS-b-P4VP based complexes-by using 488 nm linearly polarized light and characterized through birefringence and dichroism measurements. High and, stable values of birefringence are obtained for polymers with azobenzene content as low as 2.7 wt %, thus demonstrating the benefits of preorganization in photoactive dendritic moieties in side-chain H-bonded materials.