5-(trimethylsilyl)-2,2'-bi(thieno[3,2-b]thiophenyl) 4,4-dioxide | 1059190-86-1

• 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-(trimethylsilyl)-2,2'-bi(thieno[3,2-b]thiophenyl) 4,4-dioxide
• 英文别名: (4,4-Dioxo-2-thieno[3,2-b]thiophen-5-ylthieno[3,2-b]thiophen-5-yl)-trimethylsilane；(4,4-dioxo-2-thieno[3,2-b]thiophen-5-ylthieno[3,2-b]thiophen-5-yl)-trimethylsilane
• CAS: 1059190-86-1
• 化学式: C₁₅H₁₄O₂S₄Si
• 分子量: 382.624
• InChiKey: KVCXEZUHQXBZJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(trimethylsilyl)-2,2'-bi(thieno[3,2-b]thiophenyl) 4,4-dioxide 在 potassium fluoride 、 18-冠醚-6 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.0h， 以83%的产率得到2,2'-bi(thieno[3,2-b]thiophenyl) 4,4-dioxide
  参考文献：
  名称：

  Regiochemical Effects of Sulfur Oxidation on the Electronic and Solid-State Properties of Planarized Oligothiophenes Containing Thieno[3,2-b]thiophene Units

  摘要：

  The effect of position and degree of sulfur oxidation on the fundamental properties of a series of planarized thieno[3,2-b]thiophene S,S-dioxides derivatives was studied. The optical data reveal a red shift in the longest wavelength of absorption relative to the nonoxidized analogues that is indicative of a reduced HOMO-LUMO gap. The position of oxidation rather than the extent of oxidation is the most critical factor in controlling electronic properties. Single-crystal analysis reveals that some of the oligothiophene S,S-dioxides studied present pi-pi interactions which are completely absent in the nonoxidized analogue.

  DOI：

  10.1021/jo801619q
• 作为产物：
  描述：

  5-bromo-2-(trimethylsilyl)thieno[3,2-b]thiophene 1,1-dioxide 、 (噻吩并[3,2-B]噻吩-2-基)三丁基锡 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 以79%的产率得到5-(trimethylsilyl)-2,2'-bi(thieno[3,2-b]thiophenyl) 4,4-dioxide
  参考文献：
  名称：

  Regiochemical Effects of Sulfur Oxidation on the Electronic and Solid-State Properties of Planarized Oligothiophenes Containing Thieno[3,2-b]thiophene Units

  摘要：

  The effect of position and degree of sulfur oxidation on the fundamental properties of a series of planarized thieno[3,2-b]thiophene S,S-dioxides derivatives was studied. The optical data reveal a red shift in the longest wavelength of absorption relative to the nonoxidized analogues that is indicative of a reduced HOMO-LUMO gap. The position of oxidation rather than the extent of oxidation is the most critical factor in controlling electronic properties. Single-crystal analysis reveals that some of the oligothiophene S,S-dioxides studied present pi-pi interactions which are completely absent in the nonoxidized analogue.

  DOI：

  10.1021/jo801619q

文献信息

• Regiochemical Effects of Sulfur Oxidation on the Electronic and Solid-State Properties of Planarized Oligothiophenes Containing Thieno[3,2-<i>b</i>]thiophene Units
  作者：Lidaris San Miguel、Adam J. Matzger

  DOI：10.1021/jo801619q

  日期：2008.10.17

  The effect of position and degree of sulfur oxidation on the fundamental properties of a series of planarized thieno[3,2-b]thiophene S,S-dioxides derivatives was studied. The optical data reveal a red shift in the longest wavelength of absorption relative to the nonoxidized analogues that is indicative of a reduced HOMO-LUMO gap. The position of oxidation rather than the extent of oxidation is the most critical factor in controlling electronic properties. Single-crystal analysis reveals that some of the oligothiophene S,S-dioxides studied present pi-pi interactions which are completely absent in the nonoxidized analogue.