6-hexyloxy-naphthalen-2-ol | 188534-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-hexyloxy-naphthalen-2-ol
• 英文别名: 6-hexyloxy-2-hydroxynaphthalene；6-Hexoxynaphthalen-2-ol
• CAS: 188534-17-0
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: ISZLMHOXJPQHQP-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C
• 沸点：
  396.5±15.0 °C(predicted)
• 密度：
  1.069±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hexyloxy-naphthalen-2-ol 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Segregated assemblies in bridged electron-rich and electron-poor π-conjugated moieties

  摘要：

  我们报道了一种利用相互排斥的脂肪族氟碳化合物与碳氢化合物之间的相互作用，实现富电子和缺电子的π共轭基团自发分离的通用策略。

  DOI：

  10.1039/b610565c
• 作为产物：
  描述：

  2,6-萘二酚 、 1-碘己烷 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以32%的产率得到6-hexyloxy-naphthalen-2-ol
  参考文献：
  名称：

  Segregated assemblies in bridged electron-rich and electron-poor π-conjugated moieties

  摘要：

  我们报道了一种利用相互排斥的脂肪族氟碳化合物与碳氢化合物之间的相互作用，实现富电子和缺电子的π共轭基团自发分离的通用策略。

  DOI：

  10.1039/b610565c

文献信息

• Blue Luminescent Naphthalene-based Liquid Crystals
  作者：Takeshi Mori、Masashi Kijima

  DOI：10.1246/cl.2007.710

  日期：2007.6.5

  Novel luminescent liquid crystals were synthesized by introducing a mesogenic cyanobiphenylyl side chain to a luminescent naphthalene core. The 1,5-naphthalene derivatives were thermotropic liquid crystals showing monotropic phase transition, while 2,6-naphthalene derivatives showed an enantiotropic behavior. All compounds had an intense bluish emission in the solid, liquid crystal, and isotropic liquid states, which was investigated by UV–vis and PL spectroscopies.

  通过将一种介质性氰基联苯侧链引入发光萘核心，合成了新型发光液晶。1,5-萘衍生物是具有单调相变的热致液晶，而2,6-萘衍生物则表现出外消旋行为。所有化合物在固态、液晶态和各向同性液态下均具有强烈的蓝色发光，这通过紫外-可见光和荧光光谱进行了研究。
• Synthesis of soluble polyimide derived from novel naphthalene diamines for liquid crystal alignment layers and a preliminary study on the mechanism of imidization
  作者：Senlin Xia、Zhen Sun、Longfei Yi、Yinghan Wang

  DOI：10.1039/c3ra42098a

  日期：——

  Novel functional diamine, 6-hexyloxy-naphthalen-3′,5′-diaminobenzoate (N6) containing a rigid naphthalene unit, was molecularly designed and successfully synthesized. PIs (polyimides) were obtained by copolymerization of N6, 3,3′-dimethyl-4,4′-methylenediamine (DMMDA) and 4,4′-oxydiphthalic anhydride (ODPA). The structures of the intermediates, diamines and PIs were confirmed by FT-IR and 1H NMR spectra. All PIs obtained could be dissolved in polar aprotic solvents and low-boiling-point solvents. PI (polyimide) films attained using a casting method showed favorably high transmittance above 95% in the wave length range of 400–700 nm and could align LCs vertically before and after rubbing treatment. PI–N6 derived from N6, DMMDA and ODPA exhibited a much higher temperature at a 5% weight loss (T5) compared with the corresponding PI–C6 from 4-hexyloxy-biphenyl-3′,5′-diaminobenzoate (C6). For PI–N6, the weight ratio of the side chains was smaller than that of PI–C6, but a much higher T5 was attained. The results demonstrated that the introduction of a naphthalene unit into the side chain could effectively improve the thermal stability of PI without sacrificing its solubility. Moreover, the outstanding thermal stability of the PIs was explained in a preliminary manner by the imidization reaction mechanism.

  通过分子设计成功合成了含有刚性萘单元的新型功能二胺--6-己氧基萘-3′,5′-二氨基苯甲酸酯（N6）。通过 N6、3,3′-二甲基-4,4′-亚甲基二胺（DMMDA）和 4,4′-氧代双邻苯二甲酸酐（ODPA）的共聚得到了 PI（聚酰亚胺）。通过傅立叶变换红外光谱和 1H NMR 光谱确认了中间体、二胺和 PI 的结构。获得的所有 PI 都能溶解在极性钝化溶剂和低沸点溶剂中。采用浇铸法获得的 PI（聚酰亚胺）薄膜在 400-700 纳米波长范围内具有 95% 以上的高透光率，并能在摩擦处理前后使 LC 垂直排列。与由 4-己氧基联苯-3′,5′-二氨基苯甲酸酯（C6）制备的相应 PI-C6 相比，由 N6、DMMDA 和 ODPA 制备的 PI-N6 在重量损失 5%（T5）时显示出更高的温度。对于 PI-N6，侧链的重量比比 PI-C6 小，但 T5 却高得多。结果表明，在侧链中引入萘单元可有效提高 PI 的热稳定性，而不会牺牲其溶解性。此外，亚胺化反应机理也初步解释了 PIs 出色的热稳定性。
• Synthesis and Optical Properties of Luminescent Naphthalene-based Liquid Crystals
  作者：Takeshi Mori、Masashi Kijima

  DOI：10.1080/15421400802219254

  日期：2008.9.2

  Luminescent naphthalene-based liquid crystals were newly synthesized and changes of the luminescent color through the phase transitions were characterized. We prepared the compounds by combining naphthalene and known mesogenic cores, oxadiazole and fluorocyanobiphenyl, using methylene spacers. Both oxadiazole-naphthalene and fluorocyanobiphenyl-naphthalene series showed bluish luminescence in all phases. Among them, the emission peaks of 3-fluoro-4-cyano-4 '-[8-(6-hexyloxy-2-naphthyloxy)octyloxy]biphenyl in the liquid crystal and isotropic liquid states showed significant red shifts compared to that in the crystal state, which was due to specific interaction between the electron rich naphthalene and electron deficient fluorocyanobiphenyl cores.