2,8-dibromo-5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene | 1283076-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,8-dibromo-5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene
• 英文别名: 4,14-Dibromo-9-hexadecyl-3,8,15-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,13-hexaene；4,14-dibromo-9-hexadecyl-3,8,15-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,13-hexaene
• CAS: 1283076-44-7
• 化学式: C₂₈H₃₆Br₂S₃
• 分子量: 628.6
• InChiKey: TWXUUWZHPHHQSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.3
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-己基-2-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)噻吩 、 2,8-dibromo-5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene 在 四(三苯基膦)钯 、 Aliquat 336 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Benzotrithiophene Copolymers: Influence of Molecular Packing and Energy Levels on Charge Carrier Mobility

  摘要：

  The planar benzotrithiophene unit (BTT) was incorporated into four different donor polymers, and by systematically changing the nature and positioning of the solubilizing alkyl side chains along the conjugated backbone, the polymers' frontier energy levels and optoelectronic properties were controlled. Reducing the steric hindrance along the polymer backbone lead to strong interchain aggregation and highly ordered thin films, achieving hole mobilities of 0.04 cm2/(V s) in organic thin film transistors. In an attempt to increase the polymer's processability and reduce chain aggregation, steric hindrance between alkyl side chains was exploited. As a result of the increased solubility, the film forming properties of the polymer could be improved, but at the cost of reduced hole mobilities in OFET devices, due to the lack of long-range order in the polymer films.

  DOI：

  10.1021/ma500163u
• 作为产物：
  描述：

  2,3-dibromo-5-hexadecanoylthiophene 在 四(三苯基膦)钯 、 三氟化硼乙醚 、 叔丁基锂 、 sodium carbonate 、 一水合肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 正戊烷 、 二乙二醇 为溶剂， 反应 22.5h， 生成 2,8-dibromo-5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene
  参考文献：
  名称：

  Benzotrithiophene - A Planar, Electron-Rich Building Block for Organic Semiconductors

  摘要：

  Several functionalized benzo[1,2-b:3,4-b':5,6-d']trithiophenes have been synthesized and characterized. The fully planar and highly electron-rich material shows great promise as the donor constituent in donor-acceptor type copolymers for use in organic electronics. As a proof of concept, a copolymer with the electron acceptor, 2,1,3-benzothiadiazole, has been prepared. Side-chain modifications have been employed to adjust both the electron-rich character of the monomer and the solubility and processability of the polymer.

  DOI：

  10.1021/ol200643z