3-terphenyl-4-yl-5-phenylthiophene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-terphenyl-4-yl-5-phenylthiophene
• 英文别名: 2-Phenyl-4-[4-(4-phenylphenyl)phenyl]thiophene；2-phenyl-4-[4-(4-phenylphenyl)phenyl]thiophene
• 化学式: C₂₈H₂₀S
• 分子量: 388.533
• InChiKey: BAYOHZZKRRPSJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-bromo-2-phenylthiophene 在 四(三苯基膦)钯 、 magnesium 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 33.17h， 生成 3-terphenyl-4-yl-5-phenylthiophene
  参考文献：
  名称：

  Javelin-, Hockey Stick-, and Boomerang-Shaped Liquid Crystals. Structural Variations on p-Quinquephenyl

  摘要：

  The ramifications of changing molecular geometry in a series of all-aromatic liquid crystals derived from p-quinquephenyl are reported. Substituting heterocyclic rings such as thiophene, oxadiazole, oxazole, or 1,3-phenylene into the p-quinquephenylene core affects molecular shape changes via the substituent's exocyclic bond angle. In general, we found that introducing nonlinearity into molecules depresses the melting transition temperature. The symmetric (boomerang-shaped) molecules, 2,5-bisbiphenyl-4-yl-1,3,4-oxadiazole, 2,5-bisbiphenyl-4-yl-oxazole, and 1,3-bisbiphenyl-4-yl-benzene, melt into isotropic phases showing small monotropic mesophases. By contrast, the asymmetric (hockey stick-shaped) mesogens, 2-terphenyl-4-yl-5-phenyl thiophene and 2-terphenyl-4-yl-5-phenyl-1,3,4-oxadiazole, exhibit more stable enantiotropic liquid crystalline phases. The hockey stick-shaped mesogens exhibit a smectic phase as well as a nematic phase. High-temperature X-ray determination of the smectic layer spacing gives an unambiguous picture of interdigitated, bilayerlike supramolecular architecture in the smectic phase. There are associated changes in the mesogen's electrostatic profile when a heterocycle is introduced into the quinquiphenylene framework (e.g., conjugation is perturbed). Our findings suggest that steric packing considerations dominate the phase preferences (nematic versus smectic phases), However, electronic considerations (conjugation) appear to control the range of mesomorphism in this new family of nonlinear liquid crystals.

  DOI：

  10.1021/jp010869j

文献信息

• Javelin-, Hockey Stick-, and Boomerang-Shaped Liquid Crystals. Structural Variations on <i>p</i>-Quinquephenyl
  作者：Theo J. Dingemans、N. Sanjeeva Murthy、Edward T. Samulski

  DOI：10.1021/jp010869j

  日期：2001.9.1

  The ramifications of changing molecular geometry in a series of all-aromatic liquid crystals derived from p-quinquephenyl are reported. Substituting heterocyclic rings such as thiophene, oxadiazole, oxazole, or 1,3-phenylene into the p-quinquephenylene core affects molecular shape changes via the substituent's exocyclic bond angle. In general, we found that introducing nonlinearity into molecules depresses the melting transition temperature. The symmetric (boomerang-shaped) molecules, 2,5-bisbiphenyl-4-yl-1,3,4-oxadiazole, 2,5-bisbiphenyl-4-yl-oxazole, and 1,3-bisbiphenyl-4-yl-benzene, melt into isotropic phases showing small monotropic mesophases. By contrast, the asymmetric (hockey stick-shaped) mesogens, 2-terphenyl-4-yl-5-phenyl thiophene and 2-terphenyl-4-yl-5-phenyl-1,3,4-oxadiazole, exhibit more stable enantiotropic liquid crystalline phases. The hockey stick-shaped mesogens exhibit a smectic phase as well as a nematic phase. High-temperature X-ray determination of the smectic layer spacing gives an unambiguous picture of interdigitated, bilayerlike supramolecular architecture in the smectic phase. There are associated changes in the mesogen's electrostatic profile when a heterocycle is introduced into the quinquiphenylene framework (e.g., conjugation is perturbed). Our findings suggest that steric packing considerations dominate the phase preferences (nematic versus smectic phases), However, electronic considerations (conjugation) appear to control the range of mesomorphism in this new family of nonlinear liquid crystals.