2,5-dibromo-3,6-dihexadecylthieno[3,2-b]thiophene | 924894-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 2,5-dibromo-3,6-dihexadecylthieno[3,2-b]thiophene
• CAS: 924894-93-9
• 化学式: C₃₈H₆₆Br₂S₂
• 分子量: 746.882
• InChiKey: XUHHAXQNNCPYLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.5
• 重原子数：
  42
• 可旋转键数：
  30
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,3-dihydrothieno[3,4-b][1,4]dithiin-5-yl)trimethylstannane 、 2,5-dibromo-3,6-dihexadecylthieno[3,2-b]thiophene 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以61%的产率得到5,5'-(3,6-dihexadecylthieno[3,2-b]thiophene-2,5-diyl)bis(2,3-dihydrothieno[3,4-b][1,4]dithiine)
  参考文献：
  名称：

  Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-b]thiophene End-Capped with EDOT and EDTT Units

  摘要：

  The synthesis of three novel thiophene-based conjugated molecules (1-3) is presented. We report the electronic and redox properties of these compounds along with the corresponding electrochemically prepared polymers. The structures of compounds 1 and 2 have been confirmed by single-crystal X-ray diffraction studies. Noncovalent S center dot center dot center dot O interactions in 1 act to hold the molecule in a planar conformation and this is in stark contrast to the twisted nature of the 3,4-ethylenedithiothiophene (EDTT) analogue. The degree of planarity within the molecules dictates the effective conjugation length within the materials and also the packing of the molecules in the solid state. CGL-TOF studies give hole mobilities up to 4 x 10(-5) cm(2) V-1 s(-1) for compound 1 and 1.5 x 10(-5) cm(2) V-1 s(-1) for 2.

  DOI：

  10.1021/cm100514r

文献信息

• Process for the polymerisation of thiophene or selenophene derivatives
  申请人：Merck Patent GmbH

  公开号：EP1754736B1

  公开（公告）日：2011-05-11
• US8501902B2
  申请人：——

  公开号：US8501902B2

  公开（公告）日：2013-08-06
• Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-<i>b</i>]thiophene End-Capped with EDOT and EDTT Units
  作者：Greg J. McEntee、Peter J. Skabara、Filipe Vilela、Steven Tierney、Ifor D. W. Samuel、Salvatore Gambino、Simon J. Coles、Michael B. Hursthouse、Ross W. Harrington、William Clegg

  DOI：10.1021/cm100514r

  日期：2010.5.11

  The synthesis of three novel thiophene-based conjugated molecules (1-3) is presented. We report the electronic and redox properties of these compounds along with the corresponding electrochemically prepared polymers. The structures of compounds 1 and 2 have been confirmed by single-crystal X-ray diffraction studies. Noncovalent S center dot center dot center dot O interactions in 1 act to hold the molecule in a planar conformation and this is in stark contrast to the twisted nature of the 3,4-ethylenedithiothiophene (EDTT) analogue. The degree of planarity within the molecules dictates the effective conjugation length within the materials and also the packing of the molecules in the solid state. CGL-TOF studies give hole mobilities up to 4 x 10(-5) cm(2) V-1 s(-1) for compound 1 and 1.5 x 10(-5) cm(2) V-1 s(-1) for 2.