cis-4-dimethylaminoazobenzene | 25548-36-1

• 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: cis-4-dimethylaminoazobenzene
• 英文别名: 4-(dimethylamino)azobenzene；Methyl yellow
• CAS: 25548-36-1
• 化学式: C₁₄H₁₅N₃
• 分子量: 225.293
• InChiKey: JCYPECIVGRXBMO-NXVVXOECSA-N

物化性质

• 沸点：
  371.1±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  27.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-4-dimethylaminoazobenzene 以 苯 为溶剂， 生成 4-(dimethylamino)azobenzene
  参考文献：
  名称：

  Photochromic reaction in a molecular glass as a novel host matrix: the 4-dimethylaminoazobenzene-4,4′,4″-tris[3-methylphenyl(phenyl)amino]triphenylamine system

  摘要：

  为了明确分子玻璃作为新型宿主基质的特性并获得分子玻璃微观结构的信息，我们研究了 4,4â²,4â²â²-三[3-甲基苯基（苯基）氨基]三苯胺（m-MTDATA）新型分子玻璃中 4-二甲基氨基偶氮苯（DAAB）的光致变色行为，并将其与聚苯乙烯玻璃基质和苯溶液中的行为进行了比较。研究发现，在 m-MTDATA 玻璃基质中，DAAB 在光静止态的光异构化顺式异构体的比例比在聚苯乙烯基质和苯溶液中要小，而且 DAAB 的反向顺反热异构化的表观初始速率常数在 m-MTDATA 玻璃中比在聚苯乙烯基质和苯溶液中要大得多。这些结果表明，m-MTDATA 分子玻璃中局部自由体积的平均大小小于聚苯乙烯玻璃。

  DOI：

  10.1039/a805735d
• 作为产物：
  描述：

  4-(dimethylamino)azobenzene 70.0 ℃ 、30.0 MPa 条件下， 生成 cis-4-dimethylaminoazobenzene
  参考文献：
  名称：

  偶氮苯的热异构化。三、取代基、溶剂和压力对推拉偶氮苯热异构化的影响

  摘要：

  研究了取代基、溶剂和压力对 4-二甲氨基-4'-硝基偶氮苯 (NDAAB) 衍生物的热顺反异构化速率的影响。2-甲基-和 2'-氯-NDAAB 异构化速度比 NDAAB 快，2'-甲基-和 2-氯-NDAAB 异构化速度比 NDAAB 慢。对于 2,2'-二甲基-和 2,2'-二氯-NDAAB，速率介于单取代的速率之间。这些发现与 4-（二甲氨基）偶氮苯 (DAAB) 衍生物的发现非常相似，在 NDAAB 和 DAAB 之间没有观察到动力学取代基效应的根本差异。活化体积为负值，随溶剂和取代基的不同而显着变化；它的大小通常随着溶剂极性的增加而增加。即使对于 DAAB 和 4，4'-双（二乙氨基）偶氮苯 (BDEAAB)，极性溶剂中的外部压力可明显加快该速率。得出的结论是，观察到的结果与逆...

  DOI：

  10.1246/bcsj.57.1617

文献信息

• The Thermal Isomerization of Azobenzenes. III. Substituent, Solvent, and Pressure Effects on the Thermal Isomerization of Push-pull Azobenzenes
  作者：Norio Nishimura、Shinya Kosako、Yoshimi Sueishi

  DOI：10.1246/bcsj.57.1617

  日期：1984.6

  4-(dimethylamino)azobenzene (DAAB) derivatives, and no fundamental difference in the kinetic-substituent effects was observed between NDAAB and DAAB. The volume of activation, which is of a negative value, varies remarkably from solvent to solvent and from substituent to substituent; its magnitude increases generally with an increase in the solvent polarity. Even for DAAB and 4,4′-bis(diethylamino)azobenzene (BDEAAB)

  研究了取代基、溶剂和压力对 4-二甲氨基-4'-硝基偶氮苯 (NDAAB) 衍生物的热顺反异构化速率的影响。2-甲基-和 2'-氯-NDAAB 异构化速度比 NDAAB 快，2'-甲基-和 2-氯-NDAAB 异构化速度比 NDAAB 慢。对于 2,2'-二甲基-和 2,2'-二氯-NDAAB，速率介于单取代的速率之间。这些发现与 4-（二甲氨基）偶氮苯 (DAAB) 衍生物的发现非常相似，在 NDAAB 和 DAAB 之间没有观察到动力学取代基效应的根本差异。活化体积为负值，随溶剂和取代基的不同而显着变化；它的大小通常随着溶剂极性的增加而增加。即使对于 DAAB 和 4，4'-双（二乙氨基）偶氮苯 (BDEAAB)，极性溶剂中的外部压力可明显加快该速率。得出的结论是，观察到的结果与逆...
• Photochromic Behavior in the Molecular Glass of 4,4′,4″-Tris(3-methylphenylphenylamino)triphenylamine
  作者：Hideyuki Nakano、Keiichi Akamatsu、Kazuyuki Moriwaki、Yasuhiko Shirota

  DOI：10.1246/cl.1996.701

  日期：1996.8

  For the purpose of gaining information on the microstructure of molecular glasses, photochromic behavior of 4-dimethylaminoazobenzene (DAAB) in the molecular glass of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA) was studied in comparison with that in a polystyrene matrix and in a benzene solution. The results strongly suggest that the local free volume in the molecular glass of m-MTDATA is smaller than that in the polystyrene glass.

  为了获得有关分子玻璃微观结构的信息，我们对 4,4′,4″-三(3-甲基苯基氨基)三苯胺（m-MTDATA）分子玻璃中 4-二甲基氨基偶氮苯（DAAB）的光致变色行为进行了研究，并将其与聚苯乙烯基体和苯溶液中的光致变色行为进行了比较。结果强烈表明，m-MTDATA 分子玻璃中的局部自由体积小于聚苯乙烯玻璃中的自由体积。
• Photochromic reaction in a molecular glass as a novel host matrix: the 4-dimethylaminoazobenzene-4,4′,4″-tris[3-methylphenyl(phenyl)amino]triphenylamine system
  作者：Kazuyuki Moriwaki、Mitsushi Kusumoto、Keiichi Akamatsu、Hideyuki Nakano、Yasuhiko Shirota

  DOI：10.1039/a805735d

  日期：——

  For the purposes of clarifying the properties of a molecular glass as a novel host matrix and gaining information on the microstructure of the molecular glass, the photochromic behavior of 4-dimethylaminoazobenzene (DAAB) in a novel molecular glass of 4,4′,4′′-tris[3-methylphenyl(phenyl)amino]triphenylamine (m-MTDATA) was investigated, and compared with its behavior in a polystyrene glass matrix and a benzene solution. It was found that the fraction of the photoisomerized cis-isomer of DAAB at the photostationary state is smaller in the m-MTDATA glass matrix than in the polystyrene matrix and the benzene solution, and that the apparent initial rate constant for the backward cis→trans thermal isomerization of DAAB is much larger in the m-MTDATA glass than in the polystyrene matrix and the benzene solution. These results suggest that the average size of local free volume in the molecular glass of m-MTDATA is smaller than that in the polystyrene glass.

  为了明确分子玻璃作为新型宿主基质的特性并获得分子玻璃微观结构的信息，我们研究了 4,4â²,4â²â²-三[3-甲基苯基（苯基）氨基]三苯胺（m-MTDATA）新型分子玻璃中 4-二甲基氨基偶氮苯（DAAB）的光致变色行为，并将其与聚苯乙烯玻璃基质和苯溶液中的行为进行了比较。研究发现，在 m-MTDATA 玻璃基质中，DAAB 在光静止态的光异构化顺式异构体的比例比在聚苯乙烯基质和苯溶液中要小，而且 DAAB 的反向顺反热异构化的表观初始速率常数在 m-MTDATA 玻璃中比在聚苯乙烯基质和苯溶液中要大得多。这些结果表明，m-MTDATA 分子玻璃中局部自由体积的平均大小小于聚苯乙烯玻璃。
• Buvari, A.; Redling, I.; Barcza, L., Zeitschrift fur physikalische Chemie (Neue Folge), 1980, vol. 120, p. 31 - 38
  作者：Buvari, A.、Redling, I.、Barcza, L.

  DOI：——

  日期：——
• Strong inhibition of cis-trans isomerization of azo compounds by hydroxide ion
  作者：Ana Sanchez、Rita H. De Rossi

  DOI：10.1021/jo00060a026

  日期：1993.4

  The thermal cis-trans isomerization rate of methyl yellow (1), p-phenyl red (2), and o-methyl red (3) in aqueous solution was measured at different hydroxide ion concentrations, and it was found that there is a very strong inhibition as the pH increases. For 1 the rate changes from 2.17 X 10(-2) s-1 at NaOH 6 x 10(-3) M to 1.0 x 10(-3) s-1 at NaOH 0.1 M. The observed rate constant for 2 was too fast for the experimental technique used at a concentration of NaOH lower than 0.01 M. These results are interpreted in terms of a much faster rate of isomerization of the protonated cis compounds than the neutral ones, and values for the pK(a) and rate constants for both species are calculated.