9-(4-bromo-2,1,3-benzothiadiazole-7-yl)-1,1,6,6-tetramethyl-2,3,5,6-tetrahydro-1H,4H,11-oxa-3a-azabenzo[de]anthracen-10-one | 1375475-54-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-(4-bromo-2,1,3-benzothiadiazole-7-yl)-1,1,6,6-tetramethyl-2,3,5,6-tetrahydro-1H,4H,11-oxa-3a-azabenzo[de]anthracen-10-one
• 英文别名: 5-(4-Bromo-2,1,3-benzothiadiazol-7-yl)-10,10,16,16-tetramethyl-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraen-4-one
• CAS: 1375475-54-9
• 化学式: C₂₅H₂₄BrN₃O₂S
• 分子量: 510.454
• InChiKey: GMATVSQUTROKIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(4-bromo-2,1,3-benzothiadiazole-7-yl)-1,1,6,6-tetramethyl-2,3,5,6-tetrahydro-1H,4H,11-oxa-3a-azabenzo[de]anthracen-10-one 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 32.0h， 生成 2-cyano-3-[5'-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-9-yl)-[2,1,3-benzothiadiazole]-4-thiophen-2-yl]acrylic acid
  参考文献：
  名称：

  Novel D–A–π–A coumarin dyes containing low band-gap chromophores for dye-sensitised solar cells

  摘要：

  Coumarin dyes containing a low band-gap chromophore of benzothiadiazole, which comprises a coumarin moiety as the electron donor and a cyanoacrylic acid moiety as electron acceptor in D-A-pi-A system, were developed to use in dye-sensitised solar cells (DSSCs). The introduction of the benzothiadiazole unit into the molecular framve distinctly narrowed the band-gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), so that the absorption peak was red-shifted. As a result, a solar cell based on the HKK-CM4 sensitiser showed better photovoltaic performance with a J(SC) of 14.3 mA cm(-2), a V-OC of 0.58 V, and an FF of 0.72, corresponding to an overall conversion efficiency eta of 5.97% under standard AM 1.5 irradiation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.02.015
• 作为产物：
  描述：

  2-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)acetonitrile 、 9-醛基-8-羟基-1,1,7,7-四甲基久洛尼定 在 哌啶 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以42%的产率得到9-(4-bromo-2,1,3-benzothiadiazole-7-yl)-1,1,6,6-tetramethyl-2,3,5,6-tetrahydro-1H,4H,11-oxa-3a-azabenzo[de]anthracen-10-one
  参考文献：
  名称：

  Novel D–A–π–A coumarin dyes containing low band-gap chromophores for dye-sensitised solar cells

  摘要：

  Coumarin dyes containing a low band-gap chromophore of benzothiadiazole, which comprises a coumarin moiety as the electron donor and a cyanoacrylic acid moiety as electron acceptor in D-A-pi-A system, were developed to use in dye-sensitised solar cells (DSSCs). The introduction of the benzothiadiazole unit into the molecular framve distinctly narrowed the band-gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), so that the absorption peak was red-shifted. As a result, a solar cell based on the HKK-CM4 sensitiser showed better photovoltaic performance with a J(SC) of 14.3 mA cm(-2), a V-OC of 0.58 V, and an FF of 0.72, corresponding to an overall conversion efficiency eta of 5.97% under standard AM 1.5 irradiation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.02.015