4-[(4-Pentoxyphenyl)diazenyl]benzoic acid | 136954-79-5

• 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-Pentoxyphenyl)diazenyl]benzoic acid
• CAS: 136954-79-5；73182-71-5
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: DKXFKIBLLRRYGF-UHFFFAOYSA-N

物化性质

• 沸点：
  494.2±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(4-Pentoxyphenyl)diazenyl]benzoic acid 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  非偏振光下液相偶氮苯化合物的等温手性切换

  摘要：

  自发镜像对称性破坏是自然和人工自组装系统中手性发展的基本过程。研究了一系列基于三链偶氮苯的棒状化合物，这些化合物在层状LC相附近发生的各向同性液体中表现出镜像对称破坏。层状相和对称性破坏的液体之间的过渡受反式-顺式光异构化的影响，这使得非偏振光可以在手性和非手性状态之间进行快速且可逆的光诱导转换。

  DOI：

  10.1002/anie.201705559
• 作为产物：
  描述：

  4-(4-羟基-偶氮苯)苯甲酸乙酯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 3-戊酮 为溶剂， 生成 4-[(4-Pentoxyphenyl)diazenyl]benzoic acid
  参考文献：
  名称：

  Synthesis and Physico-Chemical Properties for 2-Oxochromen-6-yl 4-(4-Alkoxyphenylazo)benzoates

  摘要：

  This paper describes the preparation and thermal properties for homologous series of 2-oxochromen-6-yl 4-(4-alkoxyphenylazo)benzoates (compounds 1-n). Compounds 1-n show nematic phase exclusively, where the nematic-isotropic phase transition temperatures are between 293 degrees C for 1-4 and 256 degrees C for 1-8. Interestingly, compound 1-8 exhibits smectic A and re-entrant nematic phases in addition to the nematic one. The smectic A phase are characterized using a small angle X-ray diffraction study, indicating the smectic A phase has a partially bilayer molecular arrangement.

  DOI：

  10.1080/15421400903060557

文献信息

• Achiral bent-core azo compounds: effect of different types of linkage groups and their direction of linking on liquid crystalline properties
  作者：N. G. Nagaveni、Arun Roy、Veena Prasad

  DOI：10.1039/c2jm30709j

  日期：——

  We report, the design, synthesis and mesomorphic properties of six new homologous series of achiral bent-core compounds. In this study, we have investigated the effect of different types of linkage groups and their direction of linking, on the mesomorphic properties of azo functionalized compounds. The molecular structures of these newly synthesized compounds are characterized by spectroscopic methods. The liquid crystalline properties are studied using polarizing optical microscopy, differential scanning calorimetry, X-ray diffraction and electro-optical studies. We observed a variety of mesophases in these compounds, viz. N, B1, B2, SmA, SmAdPAetc. From our investigations, we found that the type and the direction of the linkage group affects the thermal range or even sometimes the nature of the mesophase itself. We have also carried out photo-induced studies on the B2 mesophase of some of the selected compounds and found that the reversal in the direction of linkage groups does affect the photochromic properties of the compounds.

  我们报告了六个新的同源系列非手性弯曲核化合物的设计、合成和介观性质。在这项研究中，我们探讨了不同类型的连接基团及其连接方向对偶氮官能团化合物中间形态性质的影响。这些新合成化合物的分子结构是通过光谱方法表征的。使用偏振光学显微镜、差示扫描量热法、X 射线衍射和电光研究了液晶特性。我们在这些化合物中观察到了多种介相，即 N、B1、B2、SmA、SmAdPA 等。通过研究，我们发现连接基团的类型和方向会影响热范围，有时甚至会影响介相本身的性质。我们还对一些选定化合物的 B2 介相进行了光诱导研究，发现连接基团方向的逆转确实会影响化合物的光致变色特性。
• 4-(4′-Alkyloxyphenylazo)benzoyl chlorides not only intermediates but photosensitive mesogens for optical switching
  作者：Joanna Jaworska、Izabela Korbecka、Andrzej Kochel、Zbigniew Galewski

  DOI：10.1016/j.molliq.2016.11.014

  日期：2017.1

  This paper presents results of our studies of a full homologous series of 4-(4′-alkyloxyphenylazo)benzoyl chlorides. Until now these compounds have been used only as intermediates for more complex materials and their properties were not investigated as acid chlorides are considered unstable and hence useless for applications. We show that they are in fact quite durable and possess liquid-crystalline

  本文介绍了我们对4-（4'-烷氧基苯基偶氮）苯甲酰氯的完全同源系列的研究结果。迄今为止，这些化合物仅用作更复杂材料的中间体，尚未研究其性能，因为酰基氯被认为是不稳定的，因此在应用中无用。我们证明它们实际上很耐久，并在很宽的温度范围内具有液晶性能。此外，该系列还证明了顺式-反式异构化的快速切换时间少于一个小时的弛豫时间，这使得这些化合物有望成为光学切换的材料。
• Switching Chirophilic Self‐assembly: From <i>meso</i> ‐structures to Conglomerates in Liquid and Liquid Crystalline Network Phases of Achiral Polycatenar Compounds
  作者：Mohamed Alaasar、Yu Cao、Yan Liu、Feng Liu、Carsten Tschierske

  DOI：10.1002/chem.202201857

  日期：2022.12

  The change of the interhelical self-assembly from enantiophilic to enantiophobic takes place by reduction of the alkyl chain length and leads to a phase transition from the achiral double gyroid via a tetragonal phase to a chiral triple network phase, associated with a transition from an achiral to a mirror symmetry broken liquid.

  螺旋间自组装从亲对映体到疏对映体的变化是通过烷基链长度的减少发生的，并导致从非手性双螺旋体通过四方相到手性三网络相的相变，与从非手性的转变相关为镜像对称破损液体。
• Bezborodov, V. S.; Bubel', O. N.; Kuz'michkin, P. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 132 - 135
  作者：Bezborodov, V. S.、Bubel', O. N.、Kuz'michkin, P. V.

  DOI：——

  日期：——