5-(4-bromophenyl)-2-(4-iodophenyl)-1,3,4-thiadiazole | 1261030-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-bromophenyl)-2-(4-iodophenyl)-1,3,4-thiadiazole
• CAS: 1261030-59-4
• 化学式: C₁₄H₈BrIN₂S
• 分子量: 443.105
• InChiKey: ASJMTUJDIKZLMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(4-bromophenyl)-2-(4-iodophenyl)-1,3,4-thiadiazole 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 生成 Ethyl 8-[4-[2-[4-[2-[4-[5-[4-[2-[2,5-dihexoxy-4-(2-pyridin-4-ylethynyl)phenyl]ethynyl]phenyl]-1,3,4-thiadiazol-2-yl]phenyl]ethynyl]-2,5-dihexoxyphenyl]ethynyl]phenoxy]octanoate
  参考文献：
  名称：

  Nonsymmetric bent-core liquid crystals based on a 1,3,4-thiadiazole core unit and their nematic mesomorphism

  摘要：

  The synthesis and thermotropic properties of novel V-shaped molecules having a central 1,3,4-thiadiazole core with a bend-angle of 160 are reported. The compounds consist of a shape-persistent oligo(phenylene ethynylene) scaffold with lateral alkyloxy substituents. One of the terminal aromatic units possesses an alkoxy chain capped by an ethyl ester group while the second terminus is a pyridyl group. They exhibit enantiotropic nematic phases and are characterized by polarized optical microscopy, differential scanning calorimetry, and X-ray diffraction. Results from conoscopy indicate a biaxial nature of the nematic phase near room temperature. DFT calculations of dipole moments and molecular polarizabilities are used to substantiate the experimental findings.

  DOI：

  10.1021/cm200643u
• 作为产物：
  描述：

  4-bromo-N'-(4-iodobenzoyl)benzoic acid hydrazide 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 96.0h， 以43%的产率得到5-(4-bromophenyl)-2-(4-iodophenyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis and mesomorphic properties of new V-shaped shape-persistent nematogens containing a thiazole or a thiadiazole bending unit

  摘要：

  我们合成了两个系列的新型 V 形分子，其中包含一个中央噻唑或噻二唑弯曲单元。这种设计基于形状持久的苯乙炔支架，这些支架以高区域选择性逐步连接到顶角约为 160°的非对称碘和溴官能化弯曲核心。分子工程的结果是，材料完全呈现向列液晶相（单向或对映）。通过偏振光学显微镜（POM）、差示扫描量热法（DSC）和 X 射线衍射法对相行为进行了研究。

  DOI：

  10.1039/b818240j

文献信息

• Low temperature enantiotropic nematic phases from V-shaped, shape-persistent molecules
  作者：Matthias Lehmann、Jens Seltmann

  DOI：10.3762/bjoc.5.73

  日期：——

  A series of V-shaped, shape-persistent thiadiazole nematogens, based on an oligo(phenylene ethynylene) scaffold with ester groups connected via alkyloxy spacers, was efficiently prepared by a two-step procedure. Phase engineering results in an optimum of the mesophase range and low melting temperature when the nematogens are desymmetrised with a butoxy and a heptyloxy spacer. The mesophases are enantiotropic and over the whole temperature range nematic. For the optimised mesogen structure, optical investigations by conoscopy monitored a uniaxial nematic phase upon cooling from the isotropic phase to room temperature (ΔT = 150 °C). X-ray studies on magnetic-field-aligned samples of this mesogen family revealed a general pattern, indicating the alignment of two molecular axes along individual directors in the magnetic field. These observations may be rationalised with larger assemblies of V-shaped molecules isotropically distributed around the direction of the magnetic field.

  一系列基于寡聚苯乙炔支架的具有酯基和烷氧基间隔连接的V形持形噁二唑向列体，通过两步法高效制备。相位工程导致当向列体通过丁氧和庚氧间隔去对称化时，具有最佳的液晶相范围和低熔点。液晶相具有对掌异构性，整个温度范围内都是向列相。对于优化的液晶相结构，通过共聚显微镜对光学性质进行研究，结果显示在从等向相冷却到室温（ΔT=150℃）时，呈现出单轴向列相。对于该向列体家族的磁场排列样品进行的X射线研究揭示了一般的模式，表明两个分子轴沿着磁场中的单个方向排列。这些观察结果可以通过大型V形分子的组装来解释，这些分子在磁场方向周围具有等向分布。