5,6-difluoro-4,7-bis(4-(2-ethylhexyl)-2-thienyl)-2,1,3-benzoselenadiazole | 1570099-15-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5,6-difluoro-4,7-bis(4-(2-ethylhexyl)-2-thienyl)-2,1,3-benzoselenadiazole
• CAS: 1570099-15-8
• 化学式: C₃₀H₃₈F₂N₂S₂Se
• 分子量: 607.734
• InChiKey: NBFLCLWPKXGBPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.94
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,6-difluoro-4,7-bis(4-(2-ethylhexyl)-2-thienyl)-2,1,3-benzoselenadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 24.0h， 以79%的产率得到4,7-bis(5-bromo-4-(2-ethylhexyl)-2-thienyl)-5,6-difluoro-2,1,3-benzoselenadiazole
  参考文献：
  名称：

  Fluorinated Benzoselenadiazole-Based Low-Band-Gap Polymers for High Efficiency Inverted Single and Tandem Organic Photovoltaic Cells

  摘要：

  We designed and synthesized two low-band-gap conjugated copolymers with alternating difluorinated benzoselenadiazole (DFDTBSe) and ethylhexyloxy (EH)- or octyldodecyloxy (OD)-substituted benzo[1,2-b:4,5-b']-dithiophene (BDT) building blocks. PEHBDT-DFDTBSe and PODBDT-DFDTBSe have optical band gap energies of 1.66 and 1.69 eV, respectively, and HOMO energy levels of -5.44 and -5.43 eV, respectively. The different alkyloxy side chains in the polymers affect the molecular packing and ordering in active-layer films blended with [6,6]-phenyl-C-71 butyric acid methyl ester (PC71BM). The PEHBDT-DFDTBSe:PC71BM film comprises predominantly "face-on" crystal structures with short pi-pi stacking distances (3.69 angstrom) while PODBDT-DFDTBSe:PC71BM has mostly "edge-on" structures according to two-dimensional grazing-incidence X-ray diffraction analysis. Bulk heterojunction solar cells were fabricated with an inverted structure of ITO/ethoxylated polyethylenimine/polymer:PC71BM/MoO3/Ag. The device fabricated using the PEHBDT-DFDTBSe:PC71BM active layer shows a maximum power conversion efficiency (PCE) of up to 5.74%, which is the highest value reported for OPVs containing benzoselenadiazole and BDT-derivative polymers. A tandem solar cell was also fabricated using PEHBDT-DFDTBSe:PC71BM and poly(3-hexylthiophene):indene-C-60-bisadduct as the top and bottom cell components, respectively; its maximum PCE was 7.15%.

  DOI：

  10.1021/ma4026493
• 作为产物：
  描述：

  4-异辛基噻吩-2-三丁基锡 、 4,7-dibromo-5,6-difluorobenzo[c][1,2,5]selenadiazole 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以50%的产率得到5,6-difluoro-4,7-bis(4-(2-ethylhexyl)-2-thienyl)-2,1,3-benzoselenadiazole
  参考文献：
  名称：

  Fluorinated Benzoselenadiazole-Based Low-Band-Gap Polymers for High Efficiency Inverted Single and Tandem Organic Photovoltaic Cells

  摘要：

  We designed and synthesized two low-band-gap conjugated copolymers with alternating difluorinated benzoselenadiazole (DFDTBSe) and ethylhexyloxy (EH)- or octyldodecyloxy (OD)-substituted benzo[1,2-b:4,5-b']-dithiophene (BDT) building blocks. PEHBDT-DFDTBSe and PODBDT-DFDTBSe have optical band gap energies of 1.66 and 1.69 eV, respectively, and HOMO energy levels of -5.44 and -5.43 eV, respectively. The different alkyloxy side chains in the polymers affect the molecular packing and ordering in active-layer films blended with [6,6]-phenyl-C-71 butyric acid methyl ester (PC71BM). The PEHBDT-DFDTBSe:PC71BM film comprises predominantly "face-on" crystal structures with short pi-pi stacking distances (3.69 angstrom) while PODBDT-DFDTBSe:PC71BM has mostly "edge-on" structures according to two-dimensional grazing-incidence X-ray diffraction analysis. Bulk heterojunction solar cells were fabricated with an inverted structure of ITO/ethoxylated polyethylenimine/polymer:PC71BM/MoO3/Ag. The device fabricated using the PEHBDT-DFDTBSe:PC71BM active layer shows a maximum power conversion efficiency (PCE) of up to 5.74%, which is the highest value reported for OPVs containing benzoselenadiazole and BDT-derivative polymers. A tandem solar cell was also fabricated using PEHBDT-DFDTBSe:PC71BM and poly(3-hexylthiophene):indene-C-60-bisadduct as the top and bottom cell components, respectively; its maximum PCE was 7.15%.

  DOI：

  10.1021/ma4026493