3,7-dibromo-2,8-bis(dodecyloxy)dibenzothiophene-S,S-dioxide | 1400800-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3,7-dibromo-2,8-bis(dodecyloxy)dibenzothiophene-S,S-dioxide
• CAS: 1400800-83-0
• 化学式: C₃₆H₅₄Br₂O₄S
• 分子量: 742.696
• InChiKey: SCLYOXMSTYBLQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.62
• 重原子数：
  43.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,7-dibromo-2,8-bis(dodecyloxy)dibenzothiophene-S,S-dioxide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以93%的产率得到3,7-dibromo-2,8-bis(dodecyloxy)dibenzothiophene
  参考文献：
  名称：

  Dibenzothiophene-Based Planar Conjugated Polymers for High Efficiency Polymer Solar Cells

  摘要：

  Three D-A alternating copolymers P1-3 with 3,7-linked 2,8-bis(alkoxy)dibenzothiophene as the donor unit and benzothiadiazole (P1 and P2) or 3,4-bis(octyloxy)benzothiadiazole (P3) as the acceptor unit have been designed and synthesized. P1-3 show two broad absorption peaks in the visible region, and the internal charge transfer (ICT) absorptions at about 530 nm in solutions and 560 nm in films of P3 are much stronger than that of P1 and P2. All the polymers show narrow band gaps below 2.0 eV and the low-lying HOMO energy levels of approximately -5.30 eV. The hole mobilities of polymer films spin-cast from 1,2-dichlorobenzene (DCB) solutions are 3.0 X 10(-4), 2.7 X 10(-4), and 2.3 X 10(-3) cm(2) V-1 s(-1) for P1, P2, and P3, respectively. Under simulated solar illumination of AM 1.5G (100 mW/cm(2)), a PCE of 4.48% with a V-oc of 0.83 V, a J(sc) of 9.30 mA/cm(2), and an FF of 0.58 has been achieved for PSCs with the P3:PC71BM blend (1:3, by weight) as the active layer in simply processed devices, whereas after the optimization, PCEs of only 1.02% and 1.71% have been obtained for P1- and P2-based devices, respectively. This is the first report on dibenzothiophene-based conjugated polymers used for high efficiency polymer solar cells, demonstrating that photovoltaic performance can be improved by fine-tuning the conjugated polymer structure.

  DOI：

  10.1021/ma301622g
• 作为产物：
  描述：

  在 盐酸 、 双氧水 、 溴 、 碘 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 水 、 丁酮 为溶剂， 反应 54.5h， 生成 3,7-dibromo-2,8-bis(dodecyloxy)dibenzothiophene-S,S-dioxide
  参考文献：
  名称：

  Dibenzothiophene-Based Planar Conjugated Polymers for High Efficiency Polymer Solar Cells

  摘要：

  Three D-A alternating copolymers P1-3 with 3,7-linked 2,8-bis(alkoxy)dibenzothiophene as the donor unit and benzothiadiazole (P1 and P2) or 3,4-bis(octyloxy)benzothiadiazole (P3) as the acceptor unit have been designed and synthesized. P1-3 show two broad absorption peaks in the visible region, and the internal charge transfer (ICT) absorptions at about 530 nm in solutions and 560 nm in films of P3 are much stronger than that of P1 and P2. All the polymers show narrow band gaps below 2.0 eV and the low-lying HOMO energy levels of approximately -5.30 eV. The hole mobilities of polymer films spin-cast from 1,2-dichlorobenzene (DCB) solutions are 3.0 X 10(-4), 2.7 X 10(-4), and 2.3 X 10(-3) cm(2) V-1 s(-1) for P1, P2, and P3, respectively. Under simulated solar illumination of AM 1.5G (100 mW/cm(2)), a PCE of 4.48% with a V-oc of 0.83 V, a J(sc) of 9.30 mA/cm(2), and an FF of 0.58 has been achieved for PSCs with the P3:PC71BM blend (1:3, by weight) as the active layer in simply processed devices, whereas after the optimization, PCEs of only 1.02% and 1.71% have been obtained for P1- and P2-based devices, respectively. This is the first report on dibenzothiophene-based conjugated polymers used for high efficiency polymer solar cells, demonstrating that photovoltaic performance can be improved by fine-tuning the conjugated polymer structure.

  DOI：

  10.1021/ma301622g