trans-4-n-octyloxy-4'-stilbazole | 116223-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-4-n-octyloxy-4'-stilbazole
• 英文别名: trans-1-(4-octyloxyphenyl)-2-(4-pyridyl)ethylene；4-octyloxy-4'-stilbazole；trans-4-octyloxy-4'-stilbazole；4-(4-Octyloxystyryl)pyridine；4-[(E)-2-(4-octoxyphenyl)ethenyl]pyridine
• CAS: 116223-49-5
• 化学式: C₂₁H₂₇NO
• 分子量: 309.451
• InChiKey: HAQSIDXOHJRODF-CMDGGOBGSA-N

物化性质

• 沸点：
  452.4±14.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-4-n-octyloxy-4'-stilbazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 trans-4-n-octyloxy-4'-stilbazole N-oxide
  参考文献：
  名称：

  Positional and Charged Effects of Heterocyclic N Atoms on Mesogenic Properties of Stilbazoles and Analogous N-Oxides

  摘要：

  The synthesis and the phase behavior of stilbazoles and corresponding N-oxides containing different positions of heterocyclic N atoms, i.e. trans-2'-, 3'-, 4'- stilbazoles and their N-oxides, are reported. Their phase transition temperatures and the mesogenic behavior were investigated through the DSC, polarizing optical microscope and X-ray diffraction (XRD) measurements. Increasing dipole moments by oxidation of stilbazoles to analogous N-oxides induces the S-A phase with an interdigitated bilayer packing. Both 2'-stilbazoles and analogous N-oxides do not possess mesogenic phases, which may be due that pi electron polarizabilities an reduced by the molecular twist originated from dipoles along the ortho-direction. Besides, the positonal effects of the N-oxides on mesogenic properties are more distinct than those of analogous stilbazoles, and new mesogenic phases have been generated by tuning the position of the N-oxide function in the charged liquid crystals. Consequently, unique mesogenic properties may he introduced through adjusting the dipolar direction and strength of the heterocyclic atoms in the molecules.

  DOI：

  10.1080/10587250008031032
• 作为产物：
  描述：

  4-辛氧基苯甲醛 在 lithium aluminium tetrahydride 、 三溴化磷 、 乙醇锂 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 xylene 为溶剂， 反应 1.5h， 生成 trans-4-n-octyloxy-4'-stilbazole
  参考文献：
  名称：

  Positional and Charged Effects of Heterocyclic N Atoms on Mesogenic Properties of Stilbazoles and Analogous N-Oxides

  摘要：

  The synthesis and the phase behavior of stilbazoles and corresponding N-oxides containing different positions of heterocyclic N atoms, i.e. trans-2'-, 3'-, 4'- stilbazoles and their N-oxides, are reported. Their phase transition temperatures and the mesogenic behavior were investigated through the DSC, polarizing optical microscope and X-ray diffraction (XRD) measurements. Increasing dipole moments by oxidation of stilbazoles to analogous N-oxides induces the S-A phase with an interdigitated bilayer packing. Both 2'-stilbazoles and analogous N-oxides do not possess mesogenic phases, which may be due that pi electron polarizabilities an reduced by the molecular twist originated from dipoles along the ortho-direction. Besides, the positonal effects of the N-oxides on mesogenic properties are more distinct than those of analogous stilbazoles, and new mesogenic phases have been generated by tuning the position of the N-oxide function in the charged liquid crystals. Consequently, unique mesogenic properties may he introduced through adjusting the dipolar direction and strength of the heterocyclic atoms in the molecules.

  DOI：

  10.1080/10587250008031032

文献信息

• Dicationic stilbazolium salts: Structural, thermal, optical, and ionic conduction properties
  作者：Pradip K. Bhowmik、Jung J. Koh、David King、Haesook Han、Benoît Heinrich、Bertrand Donnio、Daniel Zaton、Alfonso Martinez-Felipe

  DOI：10.1016/j.molliq.2021.117311

  日期：2021.11

  exhibit crystalline polymorphism, as deduced from differential scanning calorimetry, polarizing optical microscopy and variable temperature X-ray measurements. These salts were also found to be highly thermally stable with decomposition temperatures occurring well above 300 °C, and up to 367 °C for the triflimide salts, as determined by thermogravimetric analysis. UV–Vis absorption and photoluminescent properties

  合成了两个系列的新型二元二唑盐，分别含有甲苯磺酸盐和三磷脂对离子，并通过光谱技术和元素分析进行了表征。尽管这些盐具有促序结构，但它们都不是介晶性的，而是仅表现出结晶多态性，这是从差示扫描量热法、偏振光学显微镜和变温 X 射线测量推断得出的。还发现这些盐具有高度的热稳定性，分解温度远高于 300 °C，而三列酰胺盐的分解温度高达 367 °C，通过热重分析确定。在溶液和固态下检查了紫外-可见吸收和光致发光特性。它们在粉末态下表现出比在溶液中更高的绝对量子产率。通过阻抗谱评估介电响应，揭示了通过无定形区域的三列酰胺盐中短程电导率的显着值。我们的工作证明了这些新型二唑盐作为光电器件先进材料的潜力，其性能可以通过间隔物柔韧性的分子设计和反阴离子的选择来定制。
• Synthesis and characterization of luminescent tricationic salts of mesitylene and stilbazolium moieties
  作者：Tae Soo Jo、William L. McCurdy、Ontida Tanthmanatham、Tae K. Kim、Haesook Han、Pradip K. Bhowmik、Benoît Heinrich、Bertrand Donnio

  DOI：10.1016/j.molstruc.2012.03.024

  日期：2012.7

  A series of luminescent tricationic salts having mesitylene and stilbazolium moieties with various organic counterions were synthesized by using quaternization and metathesis reactions. Their chemical structures were characterized by H-1, F-19 and C-13 NMR spectroscopy, and elemental analysis. Their crystalline and amorphous properties were examined by differential scanning calorimetry, polarized optical microscopy, and variable-temperature X-ray diffraction studies. Their thermal stabilities were determined by thermogravimetric analyses, which were in the broad temperature ranges of 239-317 degrees C in nitrogen. Their optical properties were studied by UV-Vis and photoluminescent spectroscopy. The light-emission properties were dependent on the polarity of organic solvents (positive solvatochromism) but independent on the chemical structures of organic counterions. They emitted blue light in various organic solvents in a broad range of wavelengths of 470-497 nm, but emitted green light in a narrow range of wavelengths of 506-515 nm in their solid states. (C) 2012 Elsevier B.V. All rights reserved.
• Mesomorphic Metal Complexes Derived from 4-Alkyl-oxystilbazoles
  作者：Duncan W Bruce、S Christina Davis、David A Dunmur、Sarah A Hudson、Peter M Maitlis、Peter Styring

  DOI：10.1080/10587259208038507

  日期：1992.5
• Angular (cis-stilbazole) geometry in octahedral dimethyldihalidoplatinum(IV) complexes: potential as metallomesogens and X-ray structure of [PtMe2I2(NC5H4CHCHC6H4OC7H15)2]
  作者：Paul Beagley、Earl J Starr、John Bacsa、John R Moss、Alan T Hutton

  DOI：10.1016/s0022-328x(01)01332-8

  日期：2002.2

  The synthesis and characterisation of a series of octahedral dimethyldihalidoplatinum(IV) complexes of 4-alkoxy-4'-stilbazoles with the general formula [PtMe2X2(NC5H4CH=CHC6H4OR)(2)] (X = I or Br, R = n-alkyl) is described. Some of the complexes show mesogenic behaviour. The structure of the complex with X = I and R = C7H15 has been determined by X-ray crystallography, revealing a cis coordination geometry with respect to both the methyl and the substituted 4-alkoxy-4'-stilbazole (n-OST) ligands. (C) 2002 Elsevier Science B.V. All rights reserved.
• Controlled Photocyclization, Photodimerization, and Photoisomerization of Stilbazole Salts within Nafion Membranes
  作者：Xiao-Hong Li、Li-Zhu Wu、Li-Ping Zhang、Chen-Ho Tung

  DOI：10.1021/ol025615a

  日期：2002.4.1

  [GRAPHICS]Water- and methanol-swollen Nafion membranes were used as microreactors to successfully control the photochemical reaction pathway of stilbazole derivatives. Of particular interest is the production of azaphenanthrene (the product not obtainable in homogeneous solution) in high yield under high bulk concentration.