4-[(4-丁基苯基)二氮烯基]苯酚 | 103939-81-7

• 物质功能分类: 有机原料 - 重氮、偶氮或氧化偶氮化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 4-[(4-丁基苯基)二氮烯基]苯酚
• 中文别名: 4-正丁基-4'-羟基偶氮苯
• 英文名称: 4-[(4-butylphenyl)diazenyl]phenol
• 英文别名: trans-4-hydroxy-4′-butyl diazobenzene；4-((4-butylphenyl)diazenyl)phenol；4-n-butyl-4'-hydroxy-azobenzene；4-[(4-butylphenyl)azo]phenol；4-butyl-4'-hydroxyazobenzene；C4AzoOH
• CAS: 103939-81-7
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: FIWNTOUHYJJODB-ISLYRVAYSA-N

物化性质

• 熔点：
  81 °C
• 沸点：
  424.5±38.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.95
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[(4-丁基苯基)二氮烯基]苯酚 在 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 11-[4-(4-butylphenylazo)phenoxy]undecyl methacrylate
  参考文献：
  名称：

  Synthesis, Nanostructures, and Functionality of Amphiphilic Liquid Crystalline Block Copolymers with Azobenzene Moieties

  摘要：

  A series of liquid crystalline (LC) homopolymers of poly {11-[4-(4-butylphenylazo)phenoxy]undecyl moth acrylate}containing an azobenzene mesogen with different degrees of polymerization were synthesized by using the atom transfer radical polymerization (ATRP) method. The homopolymers were prepared with a range of number-average molecular weights from 6100 to 23 500 with narrow polydispersities of less than 1.17. Thermal investigation showed that the homopolymers exhibit monolayer smectic A, smectic C, and an unknown smectic X phases. The transition temperatures increase slightly with the increase of the molecular weights and level off at around 21 500. Novel amphiphilic LC-coil diblock copolymers with a defined length of a flexible poly(ethylene glycol) segment as the hydrophilic coil were also prepared by the ATRP method. The LC-coil diblock copolymers exhibit narrow polydispersities of less than 1.11. Morphologies of the thin films of the block copolymers were investigated by using transmission electron microscopy (TEM). Microphase separation with small size in the range of 10-20 nm (nanoseparated structures) was observed. Different photophysical and photochemical behaviors were observed between annealed homopolymer and block copolymer films, which is thought to be caused by the formation of nanostructures of the block copolymers.

  DOI：

  10.1021/ma011859j
• 作为产物：
  描述：

  4-正丁基苯胺 、 苯酚 在 盐酸 、 sodium nitrite 、 sodium carbonate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.08h， 生成 4-[(4-丁基苯基)二氮烯基]苯酚
  参考文献：
  名称：

  使用紫外/可见光可逆调节水溶液中偶氮苯基离子液体的电导率†

  摘要：

  从基础研究和技术的观点来看，刺激响应性材料的光诱导电导率调制非常重要。在这项工作中，合成和表征了5种新型的基于偶氮苯的光响应性离子液体，并研究了它们在水溶液中的电导率的UV / vis光调制。系统地研究了影响光响应性流体电导率调节的因素，例如光异构化效率，光调节聚集，离子液体的浓度和化学结构。发现在紫外光照射下，离子液体在水中的电导率显示出显着增加，并且阳离子中具有更短烷基间隔基的离子液体显示出更显着的光诱导电导率增强，最大增加了150％。另外，在用可见光替代照射时，溶液的电导率恢复（或非常接近）到初始值。因此，可以使用紫外线和可见光的交替照射来调节溶液的电导率。尽管在紫外/可见光照射下偶氮苯基团可逆的光异构化是电导率调制的起源，但是由于最大程度的电导率调制，水中离子液体的光调节聚集是必不可少的，因为紫外辐射会减弱，水溶液中离子液体的顺式异构体。

  DOI：

  10.1039/c8cp01617h

文献信息

• Multimodal control of liquid crystalline mesophases from surfactants with photoswitchable tails
  作者：Judith E. Houston、Elaine A. Kelly、Margarita Kruteva、Kiriaki Chrissopoulou、Nathan Cowieson、Rachel C. Evans

  DOI：10.1039/c9tc04079j

  日期：——

  weakly concentrated hyperswollen lamellar phases, the more common lyotropic lamellar and hexagonal phases, to pure thermotropic liquid crystals; all of which are accessible at room temperature. Photoisomerisation with UV light leads to the reversible destruction of the liquid crystalline phase, which can be spatially controlled through the use of a mask. This extensive study demonstrates the versatility

  功能材料的分层结构的非侵入式操纵是光电子，能量转换和存储设备以及药物输送系统发展的关键挑战。具有远距离有序和丰富的结构排列的溶致液晶长期以来一直被用作制备多孔材料的软模板。使用诸如光的外部刺激来修改模板结构的潜​​力可能会导致新的体系结构。在这里，使用小角度X射线散射和偏振光学显微镜的组合，我们破译了带有光可切换尾部的中性表面活性剂的各种结构/自组装关系，它们自组织成各种各样的溶致液晶中间相。轻便通过仔细选择烷基尾部/环氧乙烷头基的长度；（ii）专心；（iii）温度；（iv）光异构化。纳米级结构的范围从弱浓缩的超溶胀层状相，较常见的溶致层状和六方相到纯热致液晶。所有这些都可以在室温下使用。用紫外光进行光致异构化可导致液晶相的可逆破坏，可通过使用掩模在空间上进行控制。这项广泛的研究证明了中性光表面活性剂的多功能性，并为光响应模板或药物递送系统等新应用铺平了道路。
• A novel calamitic liquid crystalline oligomer composed of three non-identical mesogenic entities: synthesis and characterization
  作者：C. V. Yelamaggad、U. S. Hiremath、D. S. Shankar Rao、S. Krishna Prasad

  DOI：10.1039/a907974b

  日期：——

  The synthesis and evaluation of the mesomorphic properties of the first trimesogen consisting of three non-identical calamitic mesogenic entities have been described.

  已经描述了由三个不同的棒状介晶实体组成的第一个 trimesogen 的介晶性质的合成和评估。
• A Selective and Mild Synthetic Route to Dialkyl Phosphates
  作者：Jan B. Engberts、Johanna M. Kuiper、Ron Hulst

  DOI：10.1055/s-2003-38074

  日期：——

  A very mild synthetic route to dialkyl phosphates is described. Reaction of the appropriate alcohol with PCl3 followed by treatment with pyridine and CCl4 afforded the corresponding trichloromethyl ester. Subsequent reaction with the triethylamine salt of acetic acid followed by hydrolysis of the formed mixed anhydride under very mild conditions afforded the dialkyl phosphates in high yield.

  描述了一种非常温和的二烷基磷酸酯的合成路线。将适当的醇与PCl3反应，然后用吡啶和四氯化碳处理，得到相应的三氯甲基酯。随后与醋酸的三乙胺盐反应，再在非常温和的条件下水解生成的混合酸酐，从而高产率地得到二烷基磷酸酯。
• Semicarbazides as gel forming agents for common solvents and liquid crystals
  作者：Pia Deindörfer、Thomas Geiger、Dieter Schollmeyer、Jian Hui Ye、Rudolf Zentel

  DOI：10.1039/b510474b

  日期：——

  This paper describes the synthesis of 14 new gelling agents with semicarbazide groups as H-bonding motifs and alkyl- and/or azobenzene side groups. They gel solvents like decaline, 1,2-dichlorobenzene and toluene and liquid crystalline mixtures. X-Ray structure analysis shows that the semicarbazides are connected by H-bonds, each molecule to four neighbours. As a result a ribbon is formed with a core of H-bonded semicarbazide groups and alkyl chains sticking to the side. IR measurements show an unchanged H-bonding motif in large crystals and in the gel fibres, even in LC-mixture. During heating the gel melts (rheology), while the H-bonding motif of the crystal disappears (IR and DSC measurements). First experiments show that these gel-forming agents can be used to gel LC-phases and to stabilise the director pattern present during gel formation.

  本文描述了14种新型凝胶剂的合成，这些凝胶剂含有作氢键基元的半脲基团以及烷基和/或偶氮苯侧基。它们能够凝胶化如去氢化纳烷、1,2-二氯苯和甲苯等溶剂以及液晶混合物。X射线结构分析显示，半脲分子通过氢键连接，每个分子连接四个邻居。因此形成了一种带有氢键的半脲基团核心的带状结构，烷基链侧翼伸展。红外测量表明，在大型晶体和凝胶纤维中，氢键的结构保持不变，即使在液晶混合物中也是如此。在加热过程中，凝胶融化（流变特性），而晶体的氢键结构消失（红外和差示扫描量热法测量）。初步实验表明，这些形成凝胶的剂可以用于凝胶化液晶相，并稳定在凝胶形成过程中的指向图案。
• Rationally designed helical nanofibers via multiple non-covalent interactions: fabrication and modulation
  作者：Yiyang Lin、Andong Wang、Yan Qiao、Chen Gao、Markus Drechsler、Jianpin Ye、Yun Yan、Jianbin Huang

  DOI：10.1039/b926642a

  日期：——

  Building well-defined hierarchical architectures via supramolecular chemistry is one of the challenges in nanotechnology and is crucial to our understanding of biological self-assembly and biological phenomenon. In this work, a well-ordered one-dimensional (1 D) helix is fabricated with a novel sugar-based lipid by virtue of multiple non-covalent interactions (i.e. hydrophobic interaction, aromatic stacking, and hydrogen bond). The robust helical nanostructure is evidenced by negative-staining TEM, cryo-TEM and circular dichroism (CD). A series of amphiphilic molecules are also synthesized to explore molecular structure-performance relationship and elucidate intermolecular forces that contribute to complex architectures. Moreover, the supramolecular nanohelices in this work are demonstrated to be “smart nanostructures” which can be shaped into spherical micelles, vesicles or unfolded nanofibers by external stimuli, such as pH, light, and surfactant addition.

  通过超分子化学建立定义明确的分层体系结构是纳米技术面临的挑战之一，对于我们理解生物自组装和生物现象至关重要。在这项工作中，利用多种非共价相互作用（即疏水相互作用、芳香堆积和氢键），用一种新型糖基脂质制造出了一种有序的一维（1 D）螺旋结构。负染色 TEM、冷冻 TEM 和圆二色性（CD）都证明了这种坚固的螺旋纳米结构。此外，还合成了一系列两亲分子，以探索分子结构与性能的关系，并阐明促成复杂结构的分子间作用力。此外，这项工作中的超分子纳米褶皱被证明是 "智能纳米结构"，可在 pH 值、光和表面活性剂添加等外部刺激下形成球形胶束、囊泡或展开的纳米纤维。