4,7-bis(5-bromo-3,4-bis[2-ethylhexyloxy]-2-thienyl)-2,1,3-benzothiadiazole | 897037-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-bis(5-bromo-3,4-bis[2-ethylhexyloxy]-2-thienyl)-2,1,3-benzothiadiazole
• 英文别名: 4,7-Bis[5-bromo-3,4-bis(2-ethylhexoxy)thiophen-2-yl]-2,1,3-benzothiadiazole；4,7-bis[5-bromo-3,4-bis(2-ethylhexoxy)thiophen-2-yl]-2,1,3-benzothiadiazole
• CAS: 897037-85-3
• 化学式: C₄₆H₇₀Br₂N₂O₄S₃
• 分子量: 971.079
• InChiKey: GCFDGNNVYDZUAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.9
• 重原子数：
  57
• 可旋转键数：
  30
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,7-bis(5-bromo-3,4-bis[2-ethylhexyloxy]-2-thienyl)-2,1,3-benzothiadiazole 、 2-三丁基甲锡烷基噻吩 在 trans-bis(triphenylphosphine)palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以51%的产率得到4,7-bis(3,4-bis((2-ethylhexyl)oxy)-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Green Dioxythiophene-Benzothiadiazole Donor−Acceptor Copolymers for Photovoltaic Device Applications

  摘要：

  With the perspectiveof producing power-generating displays of various colors based on pi-conjugated semiconducting polymers, we have developed a synthetic design aimed at addressing color states commonly difficult to attain. Herein, we report on the structure-property relationships and performance in photovoltaic devices of a series of green-colored donor-acceptor (DA) pi-conjugated polymers ocmprised of electron-rich 3,4-dioxythiophenes (DOTs) and the electron-deficient 2,1,3-benzothiadiazole (BTD). In particular, the synthesis and chamical polymerization of two DOT-BTD regiosymmetric oligomers (pentamers M2 and M3), that can be chemically oxidized to yield two-band absorbing polymers with a transmission window in the 480-560 nm range hence reflecting/transmitting the color green (P2 and P3), is reported. The optical and electrocemical properties of P2 and P3 are described and compared to those of a blue-colored parent polymer (P1) obtained via the polymerization of a smaller DOT-BTD oligomeric precursor (trimer M1). The photovoltaic (PV) properties of P1-P3 were investigated in DA bulk heterojunction (BHJ) devices with PC60BM as the acceptor. P2 and P3 affored green-colored devices with up to 1.9% power conversion efficiency (PCE) under AM 1.5 G solar illumination. Taking into account the differences in polymer energy band structure, we have replaced PEDOT:PSS by MoO3 and optimized the solar-cell device configuration for the most efficient polymer derivative (P3), demonstrating up to a 2.71% PCE. Insight into the morphology and charge transport of these polymers in blends with PCBM is provided and related to the synthetic design and PV device performance.

  DOI：

  10.1021/cm903495b
• 作为产物：
  描述：

  4,7-Bis[3,4-bis(2-ethylhexoxy)thiophen-2-yl]-2,1,3-benzothiadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 4,7-bis(5-bromo-3,4-bis[2-ethylhexyloxy]-2-thienyl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Green Dioxythiophene-Benzothiadiazole Donor−Acceptor Copolymers for Photovoltaic Device Applications

  摘要：

  With the perspectiveof producing power-generating displays of various colors based on pi-conjugated semiconducting polymers, we have developed a synthetic design aimed at addressing color states commonly difficult to attain. Herein, we report on the structure-property relationships and performance in photovoltaic devices of a series of green-colored donor-acceptor (DA) pi-conjugated polymers ocmprised of electron-rich 3,4-dioxythiophenes (DOTs) and the electron-deficient 2,1,3-benzothiadiazole (BTD). In particular, the synthesis and chamical polymerization of two DOT-BTD regiosymmetric oligomers (pentamers M2 and M3), that can be chemically oxidized to yield two-band absorbing polymers with a transmission window in the 480-560 nm range hence reflecting/transmitting the color green (P2 and P3), is reported. The optical and electrocemical properties of P2 and P3 are described and compared to those of a blue-colored parent polymer (P1) obtained via the polymerization of a smaller DOT-BTD oligomeric precursor (trimer M1). The photovoltaic (PV) properties of P1-P3 were investigated in DA bulk heterojunction (BHJ) devices with PC60BM as the acceptor. P2 and P3 affored green-colored devices with up to 1.9% power conversion efficiency (PCE) under AM 1.5 G solar illumination. Taking into account the differences in polymer energy band structure, we have replaced PEDOT:PSS by MoO3 and optimized the solar-cell device configuration for the most efficient polymer derivative (P3), demonstrating up to a 2.71% PCE. Insight into the morphology and charge transport of these polymers in blends with PCBM is provided and related to the synthetic design and PV device performance.

  DOI：

  10.1021/cm903495b