6-<4-(4-methoxyphenylazo)phenoxy>-1-hexanol | 124774-91-0

• 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: 6-<4-(4-methoxyphenylazo)phenoxy>-1-hexanol
• 英文别名: 4-<4-(6-hydroxyhexyloxy)phenylazo>anisole；1-hydroxy-6-(4-methoxy-azobenzene-4'-oxy)hexane；4-(6-Hydroxy-hexyloxy)-4'-methoxy-azobenzen；4-methoxy-4'-(6-hydroxyhexyloxy)azobenzene；6-[4-[(4-Methoxyphenyl)diazenyl]phenoxy]hexan-1-ol
• CAS: 124774-91-0；123947-94-4
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: UHEPGJBOYDKVDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  501.6±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-<4-(4-methoxyphenylazo)phenoxy>-1-hexanol 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以66.3%的产率得到6-[4-(4-methoxyphenylazo)phenoxy]hexyl methacrylate
  参考文献：
  名称：

  Thermal Properties of Liquid-Crystalline Polyitaconates with Paired Mesogens

  摘要：

  制备了具有两个 4-甲氧基偶氮苯作为成对介原基团的 2-亚甲基琥珀酸盐（衣康酸盐）（2）。单体 2 与非介源单体--衣康酸双十八烷基酯 (DOI) 进行辐射均聚和共聚。成对介观均聚它肯酸酯表现出向列相，单体 2 与 DOI 的共聚物在 DOI 含量达到 25 摩尔%时也表现出介观相。本文讨论了成对介原对介相形成的促进作用。

  DOI：

  10.1246/bcsj.64.1715
• 作为产物：
  描述：

  苯酚 在 盐酸 、 potassium hydroxide 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 6-<4-(4-methoxyphenylazo)phenoxy>-1-hexanol
  参考文献：
  名称：

  含有庞大胆固醇部分的光活性偶氮苯基发色团的合成和表征

  摘要：

  摘要 本研究描述了使用酯化反应合成一系列带有庞大胆固醇侧基的偶氮苯基发色团。发色团由液晶中间相组成，中间相有 6 个或 11 个亚甲基链段作为间隔基，并带有给电子 (OCH3) 和吸电子 (NO2) 端基。通过核磁共振光谱、差示扫描量热法、偏光显微镜、吸收和光致发光光谱对目标化合物进行表征。所有具有六个或十一个亚甲基链段的偶氮苯衍生物都显示出手性向列相。我们研究了这些光致变色化合物的结构对紫外线照射下 E/Z 光异构化的影响。含有吸电子硝基 (NO2) 的发色团在黑暗中比供电子 (OCH3) 基团经历更快的 Z 到 E 异构化速度；异构化过程通过旋转机制进行。C6 溶液的自组装聚集体在 10% 水含量的 THF/水混合物中表现出增强的荧光。

  DOI：

  10.1016/j.molstruc.2012.02.032

文献信息

• Liquid-Crystalline Behavior and Configuration Change of Polyitaconates with Methoxyazobenzene as Mesogens
  作者：Kohei Shiraishi、Kazuo Sugiyama、Takayuki Otsu

  DOI：10.1246/bcsj.62.4083

  日期：1989.12

  Nematic polyitaconates having 4-methoxyazobenzene moieties as mesogen in the side chain were prepared. Thermal properties, polymer composition, and the photoinduced configuration change have been examined to suggest a possible use of the polymers for photosensitive liquid-crystalline materials.

  制备出了侧链中含有 4-甲氧基偶氮苯作为中间体的向列型聚他康酸酯。通过对热性能、聚合物组成和光诱导构型变化的研究，提出了将这些聚合物用于光敏液晶材料的可能性。
• Liquid Crystalline Polymers from Fumarates Containing Mesogenic Methoxyphenylazophenoxy Groups
  作者：Kohei Shiraishi、Kazuo Sugiyama

  DOI：10.1246/cl.1990.1697

  日期：1990.9

  Radical polymerization of three fumarates, ethyl 4-(4-methoxyphenylazo)phenyl fumarate (1), ethyl 6-[4-(4-methoxyphenylazo)phenoxy]hexyl fumarate (2), and ethyl 11-[4-(4-cyanophenoxycarbonyl)phenoxy]undecyl fumarate (3) was carried out in benzene. Monomers 2 and 3 polymerize to give nematic polyfumarates [poly(2), poly(3)], while monomer 1 gives no polymer. From the copolymerization of monomer 2 (M2) with styrene (M1) the monomer reactivity ratios r1 and r2 were found to be 0.60 and 0.06, respectively. The copolymerization of monomers 2 and 3 was also carried out in an attempt to obtain a guest-host system [poly(2/3)]. The rate of isomerization from trans- to cis-azobenzene was found to be 0.038 min−1 for poly(2/3).

  在苯中对 4-(4-甲氧基苯基偶氮)苯基富马酸乙酯 (1)、6-[4-(4-甲氧基苯基偶氮)苯氧基]富马酸乙酯 (2) 和 11-[4-(4-氰基苯氧基羰基)苯氧基]富马酸十一烷基乙酯 (3) 这三种富马酸盐进行了自由基聚合。单体 2 和 3 聚合生成向列聚富马酸盐[聚（2）、聚（3）]，而单体 1 则不生成聚合物。通过单体 2（M2）与苯乙烯（M1）的共聚，发现单体反应比 r1 和 r2 分别为 0.60 和 0.06。单体 2 和单体 3 还进行了共聚，试图获得客体-主体系统 [聚（2/3）]。发现聚（2/3）从反式偶氮苯到顺式偶氮苯的异构化速率为 0.038 min-1。
• Synthesis of azobenzene-functionalized star polymers via RAFT and their photoresponsive properties
  作者：Md. Zahangir Alam、Akihisa Shibahara、Tomonari Ogata、Seiji Kurihara

  DOI：10.1016/j.polymer.2011.06.035

  日期：2011.8

  Azobenzene-functionalized star polymers were synthesized by reversible addition fragmentation chain transfer (RAFT) polymerization. First, azobenzene-functionalized linear macro chain transfer agents (Macro-CTA) were synthesized by RAFT polymerization of 6-[4-(4'-Methoxyphenylazo)phenoxy]hexylmethacrylate (MAz6Mc) using 2-(2'-cyanopropyl)dithiobenzoate (CPDB) as RAFT agent in presence of AIBN as initiator in anisole. Subsequently, star azopolymers were synthesized by polymerization of a difunctional azomonomer, BMA2Az, with resultant Macro-CTA in presence of AIBN as initiator in anisole. Star azopolymers were characterized by GPC and spectroscopic methods. Thermal properties of star azopolymers were determined by DSC and TMA. Molecular weight versus conversion and molecular weight versus polymerization time attest to living polymerization characteristics. Photoisomerization behaviors of star azopolymers were studied by irradiation of both UV and visible light. Surface relief gratings were inscribed on star azopolymer films upon exposure to an interference pattern of (RCP + RCP) Ar+ laser. A diffraction efficiency of 20% was obtained by exposure of Star-8 K(2.6 K) polymer film to an (RCP + RCP) Ar+ laser for about 30 min. Surface relief grating structures were investigated by AFM and polarized optical microscopy. (C) 2011 Elsevier Ltd. All rights reserved.
• Moeller, Andrea; Czajka, Uta; Bergmann, Volker, Zeitschrift fur Chemie, 1987, vol. 27, # 6, p. 218 - 219
  作者：Moeller, Andrea、Czajka, Uta、Bergmann, Volker、Lindau, Juergen、Arnold, Manfred、Kuschel, Frank

  DOI：——

  日期：——