4-(4-nonyloxyphenylazo) benzoic acid | 88912-08-7

• 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-(4-nonyloxyphenylazo) benzoic acid
• 英文别名: 4-[(4-Nonoxyphenyl)diazenyl]benzoic acid
• CAS: 88912-08-7
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: HWAZOTCFSRSCGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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-nonyloxyphenylazo) benzoic acid 在 吡啶 、 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  切换亲手性自组装：从介观结构到非手性聚链化合物的液体和液晶网络相中的聚集体

  摘要：

  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。

  DOI：

  10.1002/chem.202201857
• 作为产物：
  描述：

  4-(4-羟基-偶氮苯)苯甲酸乙酯 在 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-(4-nonyloxyphenylazo) benzoic acid
  参考文献：
  名称：

  偶氮苯部分的变化指导偶氮表面活性剂的自组装和光响应行为†

  摘要：

  在这项研究中，详细研究了改变两个可比较的光响应性两亲物中偶氮苯基团的位置对其形成溶致液晶（LLC）的能力的影响。设计并合成了具有可比结构的两种光响应性两亲物，其由亲水性低聚氧乙烯单元，疏水性烷基链和光敏偶氮苯部分组成。当偶氮苯基团位于疏水性烷基链的中间时，在偶氮表面活性剂-水二元体系的各种含水量下观察到多个LLC相。相反，当偶氮苯基团直接连接到亲水域时，偶氮表面活性剂-水二元体系仅表现出层状相。还通过小角度X射线散射（SAXS），差示扫描量热法（DSC）和流变学的组合研究了这些自组织纳米结构的温度依赖性。在紫外线和可见光交替照射下，可逆偶氮表面活性剂的稀溶液中均有效地发生了偶氮苯基的反式-顺式光异构化。然而，仅具有位于烷基链中间的偶氮苯基的表面活性剂的光异构化才引起自组装结构及其本体性能的显着变化。这项研究表明光敏两亲物的自组装和光响应行为对表面活性剂分子结构内光敏部分的位置极为敏感。

  DOI：

  10.1039/c4tc00321g

文献信息

• 4-Methylresorcinol based bent-core liquid crystals with azobenzene wings – a new class of compounds with dark conglomerate phases
  作者：Mohamed Alaasar、Marko Prehm、Marcel Brautzsch、Carsten Tschierske

  DOI：10.1039/c4tc00533c

  日期：——

  Stochastic achiral symmetry breaking in soft matter systems, leading to conglomerates of macroscopically chiral domains (so-called dark conglomerate = DC phases) is of contemporary interest from a fundamental scientific point of view as well as for numerous potential applications in chirality sensing and non-centrosymmetric materials. Herein we report the synthesis and investigation of first azobenzene containing bent-core mesogens derived from 4-methylresorcinol forming DC phases with a new structure, distinct from the known fluid sponge-like distorted smectic phases as well as from the helical nano-filament phases (HNF phases, B4 phases). The effects of chain length and other structural modifications on achiral symmetry breaking were investigated. Homologues with relatively short alkyl chains form achiral intercalated lamellar LC phases (B6 phases), but on increasing the chains, these are replaced by the chiral and optically isotropic DC phases. Compounds with the longest alkyl chains form low birefringent crystalline conglomerates which represent less distorted versions of the optically isotropic DC-phases. Introducing additional peripheral substituents at both outer rings removes the DC phases. The DC phases were also removed and replaced by modulated smectic phases if the azo groups were replaced by ester units, showing that azo groups favour DC phase formation with new nanostructures, distinct from the previously known types.

  软物质体系中的随机非手性对称破缺会导致宏观手性域的集合体（即所谓的暗集合体 = DC 相），从基础科学的角度以及手性传感和非中心对称材料中的众多潜在应用来看，这种破缺具有时代意义。在此，我们报告了第一种由 4-甲基间苯二酚衍生的含弯核中间体偶氮苯的合成与研究，这些中间体形成了具有新结构的 DC 相，有别于已知的流体海绵状扭曲构造相以及螺旋状纳米纤维相（HNF 相，B4 相）。我们研究了链长和其他结构修饰对非手性对称性破坏的影响。烷基链相对较短的同系物形成了非手性夹层片状低浓相（B6 相），但随着烷基链的增加，这些同系物被手性和光学各向同性的 DC 相所取代。烷基链最长的化合物会形成低双折射结晶团块，代表光学各向同性 DC 相的较小变形版本。在两个外环上引入额外的外围取代基可以消除直流相。如果将偶氮基团替换为酯单元，则直流相也会消失，取而代之的是调制的平滑相，这表明偶氮基团有利于形成具有新纳米结构的直流相，不同于之前已知的类型。
• 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。
• 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。
• 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.