ethyl 5-amino-6-nitrobenzo[b]thiophene-2-carboxylate | 1561155-36-9

• 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: ethyl 5-amino-6-nitrobenzo[b]thiophene-2-carboxylate
• 英文别名: ethyl 5-amino-6-nitrobenzo[4,5-b]thiophene-2-carboxylate；Ethyl 5-amino-6-nitro-1-benzothiophene-2-carboxylate
• CAS: 1561155-36-9
• 化学式: C₁₁H₁₀N₂O₄S
• 分子量: 266.277
• InChiKey: GNJQKUQWSBMOFS-UHFFFAOYSA-N

物化性质

• 沸点：
  468.8±40.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-6-nitrobenzo[b]thiophene-2-carboxylate 在 盐酸 、 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 、 lithium hydroxide monohydrate 、 溴 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 水 为溶剂， 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：

  乙酸-(4-溴-5-甲基-2-硝基-苯胺) 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 乌洛托品 、 水 、 potassium carbonate 、 溶剂黄146 、 copper(II) oxide 、 过氧化苯甲酰 作用下， 生成 ethyl 5-amino-6-nitrobenzo[b]thiophene-2-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

文献信息

• 一类噻吩稠合苯并噁二唑衍生物及其合成方法
  申请人：武汉大学

  公开号：CN106810566A

  公开（公告）日：2017-06-09

  本发明涉及一类噻吩稠合苯并噁二唑衍生物及其合成方法，属于有机合成领域。本发明的噻吩稠合苯并噁二唑衍生物在各种普通有机溶剂具有良好的溶解性，具有非常强的拉电子能力及大的共轭面积，其作为有机受体单元可应用于构建不同D‑A结构的窄带隙共轭有机小分子和共轭有机聚合物，并可用于有机太阳能电池的电子受体材料和电子给体材料、有机场效应晶体管的空穴传输材料和电子传输材料。
• Designing a thiophene-fused benzoxadizole as an acceptor to build a narrow bandgap polymer for all-polymer solar cells
  作者：Yang Yang、Jiacheng Wang、Xiaowei Zhan、Xingguo Chen

  DOI：10.1039/c7ra02705b

  日期：——

  A thiophene-fused benzoxadizole unit as a new acceptor was designed and synthesized for the first time to build a D–A conjugated polymer with 4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene for all polymer solar cells.

  首次设计并合成了一种噻吩融合苯并噁唑单元作为新的受体，用于构建具有4,4,9,9-四（己基苯基）-4,9-二氢s-吲哚并[1,2-b:5,6-b']二噻吩的D-A共轭聚合物，用于所有聚合物太阳能电池。