4-(4-heptyloxyphenylazo) benzoic-acid | 138529-35-8

• 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-heptyloxyphenylazo) benzoic-acid
• 英文别名: 4-{(E)-[4-(Heptyloxy)phenyl]diazenyl}benzoic acid；4-[(4-heptoxyphenyl)diazenyl]benzoic acid
• CAS: 138529-35-8
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: JCMOMYZDZFROOS-UHFFFAOYSA-N

物化性质

• 熔点：
  266.1 °C
• 沸点：
  514.3±30.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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-heptyloxyphenylazo) benzoic-acid 在 吡啶 、 氯化亚砜 作用下， 生成 (2-Oxochromen-6-yl) 4-[(4-heptoxyphenyl)diazenyl]benzoate
  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
• 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-heptyloxyphenylazo) 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。
• New cholesteryl containing bent core liquid crystals
  作者：Cosmin-Constantin Huzum、Irina Carlescu、Gabriela Lisa、Dan Scutaru

  DOI：10.2298/jsc120810114h

  日期：——

  The paper presents the synthesis and mesomorphic behavior of two new series of bent core liquid crystalline compounds based on a 1,3-dihyd- roxybezene core and containing a cholesteryl 6-oxyhexanoate wing. The two series were obtained by esterification of the cholesteryl 6-(3-hydroxyphe- noxy)hexanoate core with some 4-(4-(n-alkyloxy)phenyl)azo}benzoic acids (n-alkyl = n-hexyl - n-dodecyl) or 4-

  本文介绍了基于1,3-二氢-氧化苯并苯并含有胆甾醇6-氧己酸酯翼的两个新系列弯曲核液晶化合物的合成和同构行为。这两个系列是通过将胆甾醇基6-（3-羟基苯氧基）己酸核心与一些4-（4-（n-烷氧基）苯基）偶氮}苯甲酸酯化而获得的（n-烷基= n-己基-n -十二烷基）或4-（4-（正烷基氧基）苯甲酰基）氧基}苯甲酸（正烷基=正己基-正癸基）。经由相应的酰氯或与二环己基碳二亚胺/ 4-（N，N-二甲基氨基）吡啶（DCC / DMAP）体系进行酯化反应。当通过差示扫描量热法和偏振光学显微镜研究时，所有合成的化合物均表现出具有近晶型织构的对映体液晶性质。各向同性和液晶向各向同性发生在相对较低的温度下（89至146°C之间）。含有偶氮-芳族连接基团的化合物呈现出最大的中间相稳定性范围（在42至87°C之间）。在中间相存在的范围内，所有研究的化合物均具有热稳定性。
• 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。
• Monotropic or enantiotropic mesophases? Liquid-crystalline and solid state polymorphism 4-Chloro-1,3-phenylene bis-[4-(4-alkyloxyphenylazo)benzoates
  作者：Izabela Niezgoda、Damian Pociecha、Zbigniew Galewski

  DOI：10.1016/j.tca.2014.04.024

  日期：2014.7

  This article presents a homologous series of bent-core molecules consisting of a 4-chlororesorcinol as a central unit and 4-[(4-alkyloxyphenyl)diazenyl]benzoic acids as wings. With the use of polarizing optical microscopy (POM), thermal analysis (TOA) and differential scanning calorimetry (DSC) the mesogenic properties were detected. Furthermore, the X-ray diffraction (XRD) measurements were also performed for selected samples. Compounds of the above mentioned series form nematic, B-6, and smectic C mesophases. An interesting phenomenon in the solid phase polymorphism was observed in some cases. In our experiment one crystalline form (CrI) melts to nematic phase while the second form (CrII)melts at higher temperature directly to isotropic phase. The solid state modification determines whether a monotropic and an enantiotropic mesophase is observed. (C) 2014 Elsevier B.V. All rights reserved.
• Hockey Stick Liquid Crystals Based on a 2,5-Asymmetric Disubstituted [1,3,4]Oxadiazole Core
  作者：Elena-Raluca Cioanca、Elena Luiza Epure、Irina Carlescu、Gabriela Lisa、Daniela Wilson、Nicolae Hurduc、Dan Scutaru

  DOI：10.1080/15421406.2011.556444

  日期：2011.4.22

  The article describes the liquid-crystalline properties of some 2,5-asymmetric disubstituted [1,3,4]oxadiazole derivatives containing an azo and an ester linkage obtained through esterification of 2-(4-methoxyphenyl)-5-(4-hydroxyphenyl)-[1,3,4]oxadiazole with a series of 4-(4-alkoxyphenyl)-benzoic acids containing 6-10 and 18 aliphatic carbon atoms. All reported compounds present liquid-crystalline properties, evidenced by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM), with nematic and smectic C type structures, with very large range of stability of mesophases (between 130 degrees C and 198 degrees C on heating and 134 degrees C and 214 degrees C on cooling).