5,5'-(4,4'-dihexadecyl-2,2'-bithiophene-5,5'-diyl)bis(2,3-dihydrothieno[3,4-b][1,4]dioxine) | 1217182-03-0

• 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: 5,5'-(4,4'-dihexadecyl-2,2'-bithiophene-5,5'-diyl)bis(2,3-dihydrothieno[3,4-b][1,4]dioxine)
• 英文别名: 5-[5-[5-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)-4-hexadecylthiophen-2-yl]-3-hexadecylthiophen-2-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxine；5-[5-[5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-4-hexadecylthiophen-2-yl]-3-hexadecylthiophen-2-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxine
• CAS: 1217182-03-0
• 化学式: C₅₂H₇₈O₄S₄
• 分子量: 895.453
• InChiKey: OPTCSYAEIUHBST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.9
• 重原子数：
  60
• 可旋转键数：
  33
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,2'-dibromo-3,3'-bis(n-hexadecyl)-5,5'-bithiophene 、 (2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannane 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63%的产率得到5,5'-(4,4'-dihexadecyl-2,2'-bithiophene-5,5'-diyl)bis(2,3-dihydrothieno[3,4-b][1,4]dioxine)
  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

• 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.