2,7-dibromo-9,9-bis(2-ethylhexyl)-9H-thieno[3,2-b]thieno[2'',3'':4',5']thieno[2',3':4,5]germolo[2,3-d]thiophene | 1421958-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 2,7-dibromo-9,9-bis(2-ethylhexyl)-9H-thieno[3,2-b]thieno[2'',3'':4',5']thieno[2',3':4,5]germolo[2,3-d]thiophene
• 英文别名: 6,14-Dibromo-10,10-bis(2-ethylhexyl)-3,7,13,17-tetrathia-10-germapentacyclo[9.6.0.02,9.04,8.012,16]heptadeca-1(11),2(9),4(8),5,12(16),14-hexaene；6,14-dibromo-10,10-bis(2-ethylhexyl)-3,7,13,17-tetrathia-10-germapentacyclo[9.6.0.02,9.04,8.012,16]heptadeca-1(11),2(9),4(8),5,12(16),14-hexaene
• CAS: 1421958-08-8
• 化学式: C₂₈H₃₆Br₂GeS₄
• 分子量: 733.256
• InChiKey: WOBDCVDLEYPUCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.74
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2,7-dibromo-9,9-bis(2-ethylhexyl)-9H-thieno[3,2-b]thieno[2'',3'':4',5']thieno[2',3':4,5]germolo[2,3-d]thiophene 、 三甲基氯化锡 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以74%的产率得到2,7-bis(trimethylstannyl)-9,9-bis(2-ethylhexyl)-9H-thieno[3,2-b]thieno[2'',3'':4',5']thieno[2',3':4,5]germolo[2,3-d]thiophene
  参考文献：
  名称：

  Fused Dithienogermolodithiophene Low Band Gap Polymers for High-Performance Organic Solar Cells without Processing Additives

  摘要：

  We report the synthesis of a novel ladder-type fused ring donor, dithienogermolodithiophene, in which two thieno[3,2-b]thiophene units are held coplanar by a bridging dialkyl germanium. Polymerization of this extended monomer with N-octylthienopyrrolodione by Stille polycondensation afforded a polymer, pDTTG-TPD, with an optical band gap of 1.75 eV combined with a high ionization potential. Bulk heterojunction solar cells based upon pDTTG-TPD:PC71BM blends afforded efficiencies up to 7.2% without the need for thermal annealing or processing additives.

  DOI：

  10.1021/ja311700u
• 作为产物：
  描述：

  噻吩并[3,2-b]噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2,7-dibromo-9,9-bis(2-ethylhexyl)-9H-thieno[3,2-b]thieno[2'',3'':4',5']thieno[2',3':4,5]germolo[2,3-d]thiophene
  参考文献：
  名称：

  Fused Dithienogermolodithiophene Low Band Gap Polymers for High-Performance Organic Solar Cells without Processing Additives

  摘要：

  We report the synthesis of a novel ladder-type fused ring donor, dithienogermolodithiophene, in which two thieno[3,2-b]thiophene units are held coplanar by a bridging dialkyl germanium. Polymerization of this extended monomer with N-octylthienopyrrolodione by Stille polycondensation afforded a polymer, pDTTG-TPD, with an optical band gap of 1.75 eV combined with a high ionization potential. Bulk heterojunction solar cells based upon pDTTG-TPD:PC71BM blends afforded efficiencies up to 7.2% without the need for thermal annealing or processing additives.

  DOI：

  10.1021/ja311700u

文献信息

• Fused Dithienogermolodithiophene Low Band Gap Polymers for High-Performance Organic Solar Cells without Processing Additives
  作者：Hongliang Zhong、Zhe Li、Florent Deledalle、Elisa Collado Fregoso、Munazza Shahid、Zhuping Fei、Christian B. Nielsen、Nir Yaacobi-Gross、Stephan Rossbauer、Thomas D. Anthopoulos、James R. Durrant、Martin Heeney

  DOI：10.1021/ja311700u

  日期：2013.2.13

  We report the synthesis of a novel ladder-type fused ring donor, dithienogermolodithiophene, in which two thieno[3,2-b]thiophene units are held coplanar by a bridging dialkyl germanium. Polymerization of this extended monomer with N-octylthienopyrrolodione by Stille polycondensation afforded a polymer, pDTTG-TPD, with an optical band gap of 1.75 eV combined with a high ionization potential. Bulk heterojunction solar cells based upon pDTTG-TPD:PC71BM blends afforded efficiencies up to 7.2% without the need for thermal annealing or processing additives.