5-amino-6-nitro-1-benzothiophene-2-carboxylic acid | 1610419-64-1

• 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: 5-amino-6-nitro-1-benzothiophene-2-carboxylic acid
• CAS: 1610419-64-1
• 化学式: C₉H₆N₂O₄S
• 分子量: 238.224
• InChiKey: NJLSSVQXGRKZTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106.46
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-amino-6-nitro-1-benzothiophene-2-carboxylic acid 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 氯化亚砜 、 tin(II) chloride dihdyrate 、 溴 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 2-butyloctyl 4,8-di(5-bromothiophen-2-yl)thieno[2,3-f ][2,1,3]benzothiadiazole-6-carboxylate
  参考文献：
  名称：

  Thiophene-Fused Benzothiadiazole: A Strong Electron-Acceptor Unit to Build D–A Copolymer for Highly Efficient Polymer Solar Cells

  摘要：

  A novel strong electron-acceptor, thieno[2,3-f-]-2,1,3-benzothiadiazole-6-carboxylate (BTT), was first designed and synthesized. By introducing two thienyl groups into BTT and then copolymerizing with thienyl group substituted benzo[1,2-b:4,5-b']dithiophene (BDTT) unit, a low band gap D A copolymer (PBTT-TBDTT) was obtained. Compared with its polymer analogue (PBT-TBDTT) with benzothiadiazole (BT) as an acceptor, PBTT-TBDTT exhibits stronger intramolecular charge transfer. Thus, it shows much broader absorption covering almost the whole visible light region (in the range of 300-850 nm) and narrower optical band gap around 1.45 eV with a large IP (ionization potential) at 5.35 eV. The maximum efficiency of PBTT-TBDTT based device reaches 6.07% which is much higher than that of PBT-TBDTT (3.24%), indicating that BTT unit is a promising electron-acceptor moiety to construct low band gap D A copolymers for PSCs with high photovoltaic performances.

  DOI：

  10.1021/cm501052a
• 作为产物：
  描述：

  N-[4-bromo-5-(bromomethyl)-2-nitrophenyl]acetamide 在 盐酸 、 lithium hydroxide monohydrate 、 乌洛托品 、 水 、 potassium carbonate 、 溶剂黄146 、 copper(II) oxide 作用下， 以 水 为溶剂， 生成 5-amino-6-nitro-1-benzothiophene-2-carboxylic acid
  参考文献：
  名称：

  Thiophene-Fused Benzothiadiazole: A Strong Electron-Acceptor Unit to Build D–A Copolymer for Highly Efficient Polymer Solar Cells

  摘要：

  A novel strong electron-acceptor, thieno[2,3-f-]-2,1,3-benzothiadiazole-6-carboxylate (BTT), was first designed and synthesized. By introducing two thienyl groups into BTT and then copolymerizing with thienyl group substituted benzo[1,2-b:4,5-b']dithiophene (BDTT) unit, a low band gap D A copolymer (PBTT-TBDTT) was obtained. Compared with its polymer analogue (PBT-TBDTT) with benzothiadiazole (BT) as an acceptor, PBTT-TBDTT exhibits stronger intramolecular charge transfer. Thus, it shows much broader absorption covering almost the whole visible light region (in the range of 300-850 nm) and narrower optical band gap around 1.45 eV with a large IP (ionization potential) at 5.35 eV. The maximum efficiency of PBTT-TBDTT based device reaches 6.07% which is much higher than that of PBT-TBDTT (3.24%), indicating that BTT unit is a promising electron-acceptor moiety to construct low band gap D A copolymers for PSCs with high photovoltaic performances.

  DOI：

  10.1021/cm501052a