Dibromo-[5-[4-dibromoboranyl-5-(5-methylthiophen-2-yl)thiophen-2-yl]-2-(5-methylthiophen-2-yl)thiophen-3-yl]borane | 939404-56-5

• 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: Dibromo-[5-[4-dibromoboranyl-5-(5-methylthiophen-2-yl)thiophen-2-yl]-2-(5-methylthiophen-2-yl)thiophen-3-yl]borane
• CAS: 939404-56-5
• 化学式: C₁₈H₁₂B₂Br₄S₄
• 分子量: 697.795
• InChiKey: WEYRBUJEOCHDQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.52
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dibromo-[5-[4-dibromoboranyl-5-(5-methylthiophen-2-yl)thiophen-2-yl]-2-(5-methylthiophen-2-yl)thiophen-3-yl]borane 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 24.0h， 以61%的产率得到[5-[4-Bis(2,4,6-trimethylphenyl)boranyl-5-(5-methylthiophen-2-yl)thiophen-2-yl]-2-(5-methylthiophen-2-yl)thiophen-3-yl]-bis(2,4,6-trimethylphenyl)borane
  参考文献：
  名称：

  有机硼烷受体取代的聚噻吩通过侧基硼酸化

  摘要：

  有机硼烷受体改性的聚噻吩是通过一种新的聚合物改性策略从甲硅烷基化聚噻吩制备的。缺电子二甲基硼基团的附着导致 LUMO 能级的显着降低，这可以通过紫外-可见吸收和发射光谱的强烈红移以及在显着低于阴极电位的循环伏安图中观察到可逆还原波来证明。用于硅烷化前体聚合物。具有缺电子硼基团的共轭聚合物的改性为制备具有电子学意义的材料提供了新的设计原理。

  DOI：

  10.1021/ja068771b
• 作为产物：
  描述：

  5,5'-diiodo-4,4'-bis(trimethylsilyl)-2,2'-bithiophene 在 tris(dibenzylideneacetone)dipalladium (0) 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 Dibromo-[5-[4-dibromoboranyl-5-(5-methylthiophen-2-yl)thiophen-2-yl]-2-(5-methylthiophen-2-yl)thiophen-3-yl]borane
  参考文献：
  名称：

  有机硼烷受体取代的聚噻吩通过侧基硼酸化

  摘要：

  有机硼烷受体改性的聚噻吩是通过一种新的聚合物改性策略从甲硅烷基化聚噻吩制备的。缺电子二甲基硼基团的附着导致 LUMO 能级的显着降低，这可以通过紫外-可见吸收和发射光谱的强烈红移以及在显着低于阴极电位的循环伏安图中观察到可逆还原波来证明。用于硅烷化前体聚合物。具有缺电子硼基团的共轭聚合物的改性为制备具有电子学意义的材料提供了新的设计原理。

  DOI：

  10.1021/ja068771b

文献信息

• Synthesis and Electronic Structure of Ferrocenylborane-Modified Quaterthiophenes and Polythiophenes
  作者：Haiyan Li、Anand Sundararaman、Thilagar Pakkirisamy、Krishnan Venkatasubbaiah、Frauke Schödel、Frieder Jäkle

  DOI：10.1021/ma1023654

  日期：2011.1.11

  Polythiophene was functionalized with redox-active ferrocenylborane pendent groups. A postpolymerization modification procedure was applied, in which silylated polythiophene was reacted with BBr3 to give a polymer with pendent BBr2 groups. The dibromoboryl functionalities were then further elaborated by first treating the intermediate with FcSnMe(3) to introduce the ferrocenyl moieties and then with an arylcopper derivative ArCu (Ar = 2,4,6-trimethylphenyl (Mes), 2,4,6-tri-isopropylphenyl (Tip)) to sterically stabilize the boron centers. Using similar methods, two quaterthiophene derivatives were also prepared. The number-average molecular weight (M-n) of the polymers was determined by gel permeation chromatography (GPC) relative to narrow PS standards to range from 9400 to 14 600 Da. The polymer structure was further confirmed by MALDI-TOF mass spectrometry and by multinuclear NMR spectroscopy. H,H-NOESY spectroscopy and single crystal X-ray diffraction experiments on the quaterthiophene derivatives were used to gain insight into the conformation of the oligomers and polymers in solution and the solid state. The electronic structure of the oligo- and polythiophenes was studied in detail by UV-vis spectroscopy and electrochemical measurements.