3,4,5-tris(3,7-dimethyloctyloxy)aniline | 913060-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4,5-tris(3,7-dimethyloctyloxy)aniline
• 英文别名: 3,4,5-Tris(3,7-dimethyloctoxy)aniline；3,4,5-tris(3,7-dimethyloctoxy)aniline
• CAS: 913060-28-3
• 化学式: C₃₆H₆₇NO₃
• 分子量: 561.933
• InChiKey: JMWLOBMLDGXQHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  40
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(3,7-dimethyloctyloxy)aniline 、 三醛基间苯三酚 以 乙醇 为溶剂， 反应 2.0h， 以72%的产率得到
  参考文献：
  名称：

  A New Class of Discotic Mesogens Derived from Tris(N-salicylideneaniline)s Existing in C_3h and C_s Keto-Enamine Forms

  摘要：

  Two series of a unique class of columnar liquid crystals derived from tris(N-salicylideneaniline)s [TSANs] in which the proton and the electron interact with each other through the H-bonding environment are reported. The synthesis is carried out by condensing 1,3,5-triformylphloroglucinol with the respective dialkoxyanilines or trialkoxyanilines. H-1 NMR and H-1-H-1 COSY NMR studies revealed their existence as an inseparable mixture of two keto-enamine tautomeric forms with C-3h and C-s rotational symmetries instead of the expected enol-imine form. The influence of the number of peripheral alkoxy tails on the columnar mesomorphic behavior is investigated by using polarizing optical microscopy, differential scanning calorimetry, and X-ray scattering. The fluid/glassy columnar states probed for a number of representative compounds confirmed the D-6h (hexagonal) or D-2h (rectangular) symmetry of the columns. The electronic absorption and emission characteristics of these compounds have been studied in both mesomorphic and solution states. Of special interest, the photoluminescence spectra of solution and fluid/ glassy two-dimensional structure evidently disclose the promising light generating capability of these new discotics systems.

  DOI：

  10.1021/jo0712650
• 作为产物：
  描述：

  二甲基-1-辛醇 在 HNO₃*SiO₂ 、 三溴化磷 、 potassium carbonate 、 甲烷 、 一水合肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.5h， 生成 3,4,5-tris(3,7-dimethyloctyloxy)aniline
  参考文献：
  名称：

  苯-1,4-二甲酰胺液晶的室温多晶型：氢键极性柱状组装

  摘要：

  多态性是一个令人着迷的研究课题，因为它使得单个分子能够实现多种功能。在这项研究中，我们展示了液晶（LC）苯-1,4-二甲酰胺（）衍生物（）的合成和多晶型行为。根据特定的热处理，可以在室温下获得两种不同的多晶型物。这些包括亚稳态玻璃柱状 (Col) 和热力学稳定的单斜晶 (Cry) 相。通过电分析，Col 多晶型物表现出显着的压电响应，而 Cry 多晶型物则显示出可忽略不计的压电信号。值得注意的是，该分子在液晶相中表现出 8 螺旋柱状组装体 (Col)，包含具有非零偶极矩的 β 构象异构体。根据密度泛函理论（DFT）计算，酰胺基相对于中心苯环倾斜25°。 Col 的压电响应与 Col 多晶型物的压电响应相当。因此，可以推断，Col多晶型物的极性特征是在冷却过程中从Col LC相转移的。模拟和光谱分析进一步表明，Col 和 Col 的轴向偏振都是由头尾相连的相邻酰胺单元之间的氢键相互作用驱动的

  DOI：

  10.1016/j.molliq.2024.124386

文献信息

• Tris(N-salicylideneanilines) [TSANs] exhibiting a room temperature columnar mesophase: synthesis and characterization
  作者：C.V. Yelamaggad、A.S. Achalkumar

  DOI：10.1016/j.tetlet.2006.07.102

  日期：2006.9

  Tris(N-salicylideneaniline) derivatives with peripheral branched alkyl chains, existing in their C-3h and C-s symmetric ketoenamine tautomeric forms, synthesized by condensing alkoxyanilines with 1,3,5-triformylphloroglucinol, display a technologically important columnar liquid crystal phase over a wide thermal interval (similar to 160 degrees C) well below and above room temperature, as established by optical and calorimetric studies. (c) 2006 Elsevier Ltd. All rights reserved.
• A New Class of Discotic Mesogens Derived from Tris(<i>N</i>-salicylideneaniline)s Existing in <i>C</i>₃<i>_h</i> and <i>C</i><i>_s</i> Keto-Enamine Forms
  作者：Channabasaveshwar V. Yelamaggad、Ammathnadu S. Achalkumar、D. S. Shankar Rao、S. Krishna Prasad

  DOI：10.1021/jo0712650

  日期：2007.10.1

  Two series of a unique class of columnar liquid crystals derived from tris(N-salicylideneaniline)s [TSANs] in which the proton and the electron interact with each other through the H-bonding environment are reported. The synthesis is carried out by condensing 1,3,5-triformylphloroglucinol with the respective dialkoxyanilines or trialkoxyanilines. H-1 NMR and H-1-H-1 COSY NMR studies revealed their existence as an inseparable mixture of two keto-enamine tautomeric forms with C-3h and C-s rotational symmetries instead of the expected enol-imine form. The influence of the number of peripheral alkoxy tails on the columnar mesomorphic behavior is investigated by using polarizing optical microscopy, differential scanning calorimetry, and X-ray scattering. The fluid/glassy columnar states probed for a number of representative compounds confirmed the D-6h (hexagonal) or D-2h (rectangular) symmetry of the columns. The electronic absorption and emission characteristics of these compounds have been studied in both mesomorphic and solution states. Of special interest, the photoluminescence spectra of solution and fluid/ glassy two-dimensional structure evidently disclose the promising light generating capability of these new discotics systems.
• Room-temperature polymorphism of a benzene-1,4-dicarboxamide liquid crystal: Hydrogen-bonded polar columnar assembly
  作者：Seongwon Park、Hee-Jae Won、Jaeduk Byun、Byoung-Ki Cho

  DOI：10.1016/j.molliq.2024.124386

  日期：2024.4

  Polymorphism is a fascinating research subject as it enables diverse functionalities to be achieved from a single molecule. In this study, we present the synthesis and polymorphic behavior of a liquid crystalline (LC) benzene-1,4-dicarboxamide () derivative (). Depending on specific thermal treatments, two distinct polymorphs can be obtained at room temperature. These include a metastable glassy columnar

  多态性是一个令人着迷的研究课题，因为它使得单个分子能够实现多种功能。在这项研究中，我们展示了液晶（LC）苯-1,4-二甲酰胺（）衍生物（）的合成和多晶型行为。根据特定的热处理，可以在室温下获得两种不同的多晶型物。这些包括亚稳态玻璃柱状 (Col) 和热力学稳定的单斜晶 (Cry) 相。通过电分析，Col 多晶型物表现出显着的压电响应，而 Cry 多晶型物则显示出可忽略不计的压电信号。值得注意的是，该分子在液晶相中表现出 8 螺旋柱状组装体 (Col)，包含具有非零偶极矩的 β 构象异构体。根据密度泛函理论（DFT）计算，酰胺基相对于中心苯环倾斜25°。 Col 的压电响应与 Col 多晶型物的压电响应相当。因此，可以推断，Col多晶型物的极性特征是在冷却过程中从Col LC相转移的。模拟和光谱分析进一步表明，Col 和 Col 的轴向偏振都是由头尾相连的相邻酰胺单元之间的氢键相互作用驱动的