1-[4-(dodecyloxy)phenyl]-1H-imidazole | 131625-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[4-(dodecyloxy)phenyl]-1H-imidazole
• 英文别名: 1-(4-(dodecyloxy)phenyl)-1H-imidazole；1-[4'-(dodecyloxy)phenyl]imidazole
• CAS: 131625-76-8
• 化学式: C₂₁H₃₂N₂O
• 分子量: 328.498
• InChiKey: MIRSXJLFNPMQSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  24.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.05
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[4-(dodecyloxy)phenyl]-1H-imidazole 在 六氟磷酸钾 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 50.33h， 生成 3-dodecyl-1-(4-(dodecyloxy)phenyl)-1H-imidazol-3-ium hexafluorophosphate
  参考文献：
  名称：

  异质微波辅助乌尔曼型方法合成硬核离子液晶

  摘要：

  我们提出了一种高效的乌尔曼型合成方法，可通过三个步骤来制备具有扩展的芳香族核的咪唑鎓化合物。该过程开始于在铜（II）掺杂的NaY沸石存在下的微波辅助，非均相催化的交叉偶联反应，从而以良好的产率直接获得咪唑-芳族衍生物。创新之处在于该反应不需要溶剂，配体或惰性气氛。随后，将这些衍生物用溴代烷烃进行烷基化，并将咪唑鎓产物的溴化物交换为[BF4] -或[PF6] -阴离子。我们已经研究了在偶联反应过程中甲基对芳族单元的影响（诱导作用）以及其对结晶态不同排列的影响。我们已经能够将这种合成扩展到显示出层状自组织（近晶A）的离子型液晶化合物。通过偏光光学显微镜（POM），差示扫描量热法（DSC）和小角X射线散射（SAXS）研究了介晶行为和相变温度。

  DOI：

  10.1039/c8nj01609g
• 作为产物：
  描述：

  咪唑 、 1-十二烷氧基-4-碘苯 在 potassium carbonate 作用下， 反应 72.0h， 以84%的产率得到1-[4-(dodecyloxy)phenyl]-1H-imidazole
  参考文献：
  名称：

  A convenient method for preparing rigid-core ionic liquid crystals

  摘要：

  一种高效、无溶剂的方法用于使用Cu(II)-NaY作为催化剂和K₂CO₃作为碱对咪唑进行N-芳基化，该方法报道了通过1-(十二氧基)-4-碘苯合成介孔相3-[4-(十二氧基)苯基]-1-甲基-1H-咪唑-3-ium碘的两步法合成，并通过偏振光学显微镜、差示扫描量热法和X射线衍射对其介相性进行了全面研究。此外，还报告了其层状晶体结构、电化学行为和UV（吸收和发射）性质。

  DOI：

  10.3762/bjoc.5.51

文献信息

• Towards room temperature ionic liquid crystals: linear versus bent imidazolium phenylpyrimidines
  作者：Gundula F. Starkulla、Simon Klenk、Martin Butschies、Stefan Tussetschläger、Sabine Laschat

  DOI：10.1039/c2jm34595a

  日期：——

  The synthesis and the mesomorphic properties of novel imidazolium salts with mesogenic 2-phenylpyrimidine or 2-alkylpyrimidinecarboxylic acid central cores are reported. The mesogenic units are connected to the imidazolium head groups via an alkoxy spacer. In order to adjust the mesomorphic properties the length of the alkoxy spacer and the terminal alkyl group, the counter ion, the substitution pattern of the imidazolium head group and the molecular geometry (linear vs. bent) are varied and the corresponding compounds were investigated in detail using differential scanning calorimetry (DSC), polarized optical microscopy (POM) and X-ray scattering (WAXS, SAXS). Whereas SmA phases with monolayer orientation were observed for imidazolium salts with short N-substituents (R = CH3, C4H9) at the imidazolium head group, the corresponding derivatives with longer N-substituents (R = C12H25, C12H25OC6H4) displayed SmA phases with bilayer orientation irrespective of a linear or bent geometry. For two derivatives, p-5(10,8) and p-5(12,8), a SmC phase was observed. Indeed, bending of the mesogenic core led to a shift of the mesophases towards lower temperatures. Several of the meta-2-phenylpyrimidine derivatives as well as 2-pyrimidine carboxylates displayed melting points below 50 °C. For 2-pyrimidine carboxylates replacement of a bromide anion by triflate resulted in a further decrease of the melting transition close to ambient temperature.

  本文报道了具有介晶2-苯基嘧啶或2-烷基嘧啶羧酸中心核的新型咪唑鎓盐的合成及其介晶性质。介晶单元通过烷氧基间隔基与咪唑鎓头部基团相连。为了调节介晶性质，变化了烷氧基间隔基和末端烷基基团的长度、反离子、咪唑鎓头部基团的取代模式和分子几何形状（线性 vs. 弯曲），并使用差示扫描量热法（DSC）、偏光光学显微镜（POM）和 X 射线散射（WAXS，SAXS）详细研究了相应的化合物。对于含有短 N-取代基（R = CH3，C4H9）的咪唑鎓盐，观察到具有单层取向的 SmA 相，而含有较长 N-取代基（R = C12H25， OC6H4）的相应衍生物显示出双层取向的 SmA 相，无论其几何形状为线性或弯曲。对于两种衍生物 p-5(10,8) 和 p-5(12,8)，观察到 SmC 相。事实上，介晶核的弯曲导致介相向较低温度偏移。多个间位-2-苯基嘧啶衍生物以及 2-嘧啶羧酸盐显示出低于 50 °C 的熔点。对于 2-嘧啶羧酸盐，用三氟甲磺酸盐替换溴化物离子进一步降低了接近室温的熔融转变温度。
• Dicationic imidazolium-based ionic liquids and ionic liquid crystals with variously positioned fluoro substituents
  作者：Xiaoju Li、Duncan W. Bruce、Jean'ne M. Shreeve

  DOI：10.1039/b912873e

  日期：——

  A series of new dicationic imidazolium-based organic salts bearing fluoro substituents on the bent-core unit and/or linker benzene-ring positions has been synthesized and characterized. The properties of these salts, including transition and decomposition temperatures, and density were determined, indicating that their performance is strongly dependent on the positions of the fluoro substituents, the number of carbon atoms in the alkyl group, and the anion present. Examination by polarized optical microscopy showed that the four salts (compounds 4c, 7a, 7b and 8b, where the alkyl group was C12H25–) were mesomorphic and these data were supported by DSC measurements.

  合成并表征了一系列新的二阳离子咪唑盐，这些盐在弯曲核心单元和/或连接苯环位置上具有氟取代基。这些盐的性质，包括相变温度、分解温度和密度得到了测定，表明它们的性能强烈依赖于氟取代基的位置、烷基链中碳原子的数量以及所含的阴离子。通过偏光显微镜的观察显示，四种盐（化合物4c、7a、7b和8b，其中烷基链为C12H25–）具有介晶性，这些数据得到了差示扫描量热法（DSC）测量的支持。
• Synthesis and Mesomorphic Properties of Rigid-Core Ionic Liquid Crystals
  作者：Paul H. J. Kouwer、Timothy M. Swager

  DOI：10.1021/ja075651a

  日期：2007.11.1

  Ionic liquid crystals combine the unique solvent properties of ionic liquids with self-organization found for liquid crystals. We report a detailed analysis of the structure-property relationship of a series of new imidazolium-based liquid crystals with an extended aromatic core. Investigated parameters include length and nature of the tails, the length of the rigid core, the lateral substitution pattern, and the nature of the counterion. Depending on the molecular structure, two mesophases were observed: a bilayered SmA(2) phase and the more common monolayered SmA phase, both strongly interdigitated. Most materials show mesophases stable to high temperatures. For some cases, crystallization could be suppressed, and room-temperature liquid crystalline phases were obtained. The mesomorphic properties of several mixtures of ionic liquid crystals were investigated. Many mixtures showed full miscibility and ideal mixing behavior; however, in some instances we observed, surprisingly, complete demixing of the component SmA phases. The ionic liquid crystals and mixtures presented have potential applications, due to their low melting temperatures, wide temperature ranges, and stability with extra ion-doping.