5''-bromo-5-tridecafluorohexyl-2,2':5',2''-terthiophene | 925424-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5''-bromo-5-tridecafluorohexyl-2,2':5',2''-terthiophene
• 英文别名: 2-Bromo-5-[5-[5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)thiophen-2-yl]thiophen-2-yl]thiophene；2-bromo-5-[5-[5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)thiophen-2-yl]thiophen-2-yl]thiophene
• CAS: 925424-89-1
• 化学式: C₁₈H₆BrF₁₃S₃
• 分子量: 645.327
• InChiKey: WNWQZQBOWYOEAC-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  423.3±45.0 °C(Predicted)
• 密度：
  1.719±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  5''-bromo-5-tridecafluorohexyl-2,2':5',2''-terthiophene 、 2-三丁基甲锡烷基噻吩 在 四(三苯基膦)钯 作用下， 以 氯苯 为溶剂， 190.0 ℃ 、15.0 kPa 条件下， 反应 0.02h， 以54%的产率得到α-perfluorohexyltetrathiophene
  参考文献：
  名称：

  Rapid synthesis and fluorous-phase purification of α-perfluorohexyloligothiophenes

  摘要：

  A high-throughput methodology that facilitates the synthesis, purification and characterisation of pi-conjugated oligothiophenes has been developed. alpha-Perfluorohexyltetrathiophene was synthesised by sequential alpha-bromination and microwave promoted Stille cross-coupling reactions. Each synthetic transformation was followed by a fluorous solid-phase extraction (F-SPE) procedure to isolate the desired alpha-perfluorohexyloligothiophene. After a single F-SPE, each oligomer gave essentially one peak by GC-MS, which enabled stepwise growth of a tetrathiophene with no additional purification of the intermediate building blocks required. We anticipate that microwave accelerated synthesis in conjunction with fluorous-phase purification of pi-conjugated systems will find generic application in the high-throughput parallel-synthesis of novel organic materials for semiconductor applications. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.165
• 作为产物：
  描述：

  alpha-三联噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5''-bromo-5-tridecafluorohexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Non-symmetrical oligothiophenes with ‘incompatible’ substituents

  摘要：

  The syntheses of oligothiophenes 1 and 2 comprising two different types of peripheral substituents, namely alkyl and perfluoroalkyl, is reported. The key synthetic step is the Pd-catalyzed cross-coupling of perfluoroalkylated bromide 3 with an appropriate boronate. This molecular design is expected to promote unusual two-layer packing, which is of interest for application in electronic devices. Quaterthiophene 1 forms smectic mesophase, though in the narrow temperature range, and is suitable for the fabrication of thin films by solution processing methods. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.029

文献信息

• Non-symmetrical oligothiophenes with ‘incompatible’ substituents
  作者：Delphine Didier、Sergey Sergeyev、Yves Henri Geerts

  DOI：10.1016/j.tet.2006.11.029

  日期：2007.1

  The syntheses of oligothiophenes 1 and 2 comprising two different types of peripheral substituents, namely alkyl and perfluoroalkyl, is reported. The key synthetic step is the Pd-catalyzed cross-coupling of perfluoroalkylated bromide 3 with an appropriate boronate. This molecular design is expected to promote unusual two-layer packing, which is of interest for application in electronic devices. Quaterthiophene 1 forms smectic mesophase, though in the narrow temperature range, and is suitable for the fabrication of thin films by solution processing methods. (c) 2006 Elsevier Ltd. All rights reserved.
• Rapid synthesis and fluorous-phase purification of α-perfluorohexyloligothiophenes
  作者：Mark C. McCairn、Michael L. Turner

  DOI：10.1016/j.tetlet.2006.11.165

  日期：2007.2

  A high-throughput methodology that facilitates the synthesis, purification and characterisation of pi-conjugated oligothiophenes has been developed. alpha-Perfluorohexyltetrathiophene was synthesised by sequential alpha-bromination and microwave promoted Stille cross-coupling reactions. Each synthetic transformation was followed by a fluorous solid-phase extraction (F-SPE) procedure to isolate the desired alpha-perfluorohexyloligothiophene. After a single F-SPE, each oligomer gave essentially one peak by GC-MS, which enabled stepwise growth of a tetrathiophene with no additional purification of the intermediate building blocks required. We anticipate that microwave accelerated synthesis in conjunction with fluorous-phase purification of pi-conjugated systems will find generic application in the high-throughput parallel-synthesis of novel organic materials for semiconductor applications. (c) 2006 Elsevier Ltd. All rights reserved.