5,7-bis(2-thienyl)thieno[3',4':5,6]-1,4-dithiino[2,3-d]-1,3-dithiole-2-thione | 241479-12-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,7-bis(2-thienyl)thieno[3',4':5,6]-1,4-dithiino[2,3-d]-1,3-dithiole-2-thione
• 英文别名: 5,7-di(2-thienyl)[1,3]dithiolo[4,5-b]thieno[3,4-e][1,4]dithiine-2-thione；10,12-Dithiophen-2-yl-2,4,6,8,11-pentathiatricyclo[7.3.0.03,7]dodeca-1(12),3(7),9-triene-5-thione
• CAS: 241479-12-9
• 化学式: C₁₅H₆S₈
• 分子量: 442.741
• InChiKey: FHLPQSZYZFOUGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  218
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 5,7-bis(2-thienyl)thieno[3',4':5,6]-1,4-dithiino[2,3-d]-1,3-dithiole-2-thione 以 氯仿 为溶剂， 反应 72.0h， 生成 2-(methylthio)-5,7-di(thiophen-2-yl)-[1,3]dithiolo[4,5-b]thieno[3,4-e][1,4]dithiin-1-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Fluorene functionalised sexithiophenes—utilising intramolecular charge transfer to extend the photocurrent spectrum in organic solar cells

  摘要：

  我们制备了一系列带有缺电子芴单元的新型低聚噻吩，并对其进行了表征。这些材料通过 C8/C11 烷基链或三乙二醇侧基实现了官能化，但高级低聚物的溶解性仍然很差。通过紫外可见光谱和光诱导吸收光谱，研究了噻吩类似物（化合物 3）的吸收特性。利用 3 和富勒烯衍生物 [6,6]-phenyl-C61 丁酸甲酯（PCBM）的混合物制作了光伏电池。该装置的光电流光谱与sexithiophene 系统的吸收光谱相匹配，后者包含一个由 1,3-二硫代-芴单元产生的分子内电荷转移带。功率转换效率为 0.1%。

  DOI：

  10.1039/b609858d
• 作为产物：
  描述：

  trans-5,6-bis(2-thienoyl)-5,6-dihydro-1,4-dithiino[2,3-d]-1,3-dithiole-2-thione 在 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以57%的产率得到5,7-bis(2-thienyl)thieno[3',4':5,6]-1,4-dithiino[2,3-d]-1,3-dithiole-2-thione
  参考文献：
  名称：

  Novel Terthiophene and Bis(thienyl)furan Derivatives as Precursors to Highly Electroactive Polymers

  摘要：

  The syntheses of a series of 1,3-dithiole-2-thione derivatives (3-6), bearing fused terthiophene or bis(2-thienyl)-2,5-furan units, are reported. These novel heterocycles are readily polymerized electrochemically to give stable electroactive materials. The target compounds were obtained in moderate to high yield via the cyclization of the corresponding diketones or hydroxyketones, using phosphorus pentasulfide or acidic conditions. The ketones 12 and 17 were prepared directly from their hydroxy precursors by treatment with MnO2. The trans configuration of diketone 20 was confirmed by X-ray crystallography.

  DOI：

  10.1021/jo990198+

文献信息

• Fluorene functionalised sexithiophenes—utilising intramolecular charge transfer to extend the photocurrent spectrum in organic solar cells
  作者：Peter J. Skabara、Rory Berridge、Igor M. Serebryakov、Alexander L. Kanibolotsky、Lyudmila Kanibolotskaya、Sergey Gordeyev、Igor F. Perepichka、N. Serdar Sariciftci、Christoph Winder

  DOI：10.1039/b609858d

  日期：——

  A new series of oligothiophenes bearing electron deficient fluorene units have been prepared and characterised. The materials are functionalised by C8/C11 alkyl chains or triethylene glycol side groups, yet the higher oligomers remain poorly soluble. The absorption characteristics of a sexithiophene analogue (compound 3) have been studied by UV-vis and photoinduced absorption spectroscopy. Photovoltaic cells have been fabricated from blends of 3 and fullerene derivative [6,6]-phenyl-C61 butyric acid methyl ester (PCBM). The photocurrent spectrum of the device matches the absorption spectrum of the sexithiophene system which incorporates an intramolecular charge transfer band arising from the 1,3-dithiole-fluorene units. A modest power conversion efficiency of 0.1% was achieved.

  我们制备了一系列带有缺电子芴单元的新型低聚噻吩，并对其进行了表征。这些材料通过 C8/C11 烷基链或三乙二醇侧基实现了官能化，但高级低聚物的溶解性仍然很差。通过紫外可见光谱和光诱导吸收光谱，研究了噻吩类似物（化合物 3）的吸收特性。利用 3 和富勒烯衍生物 [6,6]-phenyl-C61 丁酸甲酯（PCBM）的混合物制作了光伏电池。该装置的光电流光谱与sexithiophene 系统的吸收光谱相匹配，后者包含一个由 1,3-二硫代-芴单元产生的分子内电荷转移带。功率转换效率为 0.1%。
• The development of an electropolymerisable unit for TTF-thiophene fused monomers
  作者：Peter J. Skabara、Donna M. Roberts、Igor M. Serebryakov、Cristina Pozo-Gonzalo

  DOI：10.1039/b001943g

  日期：——

  A novel poly(terthiophene) species provides the first example of an annelated TTF-thiophene derivative which can be polymerised electrochemically.

  一种新型聚（四联噻吩）提供了首个环状TTF-噻吩衍生物的例子，该衍生物可通过电化学聚合。
• Novel Terthiophene and Bis(thienyl)furan Derivatives as Precursors to Highly Electroactive Polymers
  作者：Peter J. Skabara、Igor M. Serebryakov、Donna M. Roberts、Igor F. Perepichka、Simon J. Coles、Michael B. Hursthouse

  DOI：10.1021/jo990198+

  日期：1999.8.1

  The syntheses of a series of 1,3-dithiole-2-thione derivatives (3-6), bearing fused terthiophene or bis(2-thienyl)-2,5-furan units, are reported. These novel heterocycles are readily polymerized electrochemically to give stable electroactive materials. The target compounds were obtained in moderate to high yield via the cyclization of the corresponding diketones or hydroxyketones, using phosphorus pentasulfide or acidic conditions. The ketones 12 and 17 were prepared directly from their hydroxy precursors by treatment with MnO2. The trans configuration of diketone 20 was confirmed by X-ray crystallography.