2-(5-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-azabenzo[de]anthracen-9-yl)thiophene-2-yl)-5-bromo-3,4-ethylenedioxythiophene | 1313219-44-1

• 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: 2-(5-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-azabenzo[de]anthracen-9-yl)thiophene-2-yl)-5-bromo-3,4-ethylenedioxythiophene
• CAS: 1313219-44-1
• 化学式: C₂₉H₂₈BrNO₄S₂
• 分子量: 598.582
• InChiKey: VKNLXBNRDGODGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  37.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  51.91
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(5-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-azabenzo[de]anthracen-9-yl)thiophene-2-yl)-5-bromo-3,4-ethylenedioxythiophene 、 (5-(1,3-二氧杂烷-2-基)噻吩-2-基)三丁基锡 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以52%的产率得到2-(2-(5-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-azabenzo[de]anthracen-9-yl)thiophene-2-yl)-3,4-ethylenedioxythiophen-5-yl)-5-thiophenylaldehyde
  参考文献：
  名称：

  Coumarin dyes containing low-band-gap chromophores for dye-sensitised solar cells

  摘要：

  A series of coumarin dyes containing a low-band-gap chromophore of ethylenedioxythiophene (EDOT), which comprises a coumarin moiety as the electron donor and a cyanoacrylic acid moiety as electron acceptor in D-pi-A chromophores, were developed for use in dye-sensitised solar cells (DSSCs). These coumarin dyes have been used to fabricate DSSCs using I-/I-3(-) liquid electrolytes and their device performances were compared with that of NKX-2677 as a standard dye. Even though HKK-CM2 and HKK-CM3 have more extended aromatic units than HKK-CM1, the degree of pi-conjugation in HKK-CM2 and HKK-CM3 is less efficient than that of HKK-CM1, due to the relatively larger torsion angle between the plane of the donor and that of the acceptor. It is also in a good agreement with Density Functional Theory (DFT) calculations. As a result, a solar cell based on HKK-CM1 sensitiser shows better photovoltaic performance with J(SC) 0114.2 mA cm(-2), V-OC of 0.60 V, and a fill factor of 0.70, corresponding to an overall conversion efficiency eta of 6.07% under the standard AM 1.5 irradiation, than HKK-CM2 and HKK-CM3-based solar cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.01.009
• 作为产物：
  描述：

  三丁基(2,3-二氢噻吩并[3,4-b]-[1,4]二恶英-5-基)锡烷 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 2-(5-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-azabenzo[de]anthracen-9-yl)thiophene-2-yl)-5-bromo-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  Coumarin dyes containing low-band-gap chromophores for dye-sensitised solar cells

  摘要：

  A series of coumarin dyes containing a low-band-gap chromophore of ethylenedioxythiophene (EDOT), which comprises a coumarin moiety as the electron donor and a cyanoacrylic acid moiety as electron acceptor in D-pi-A chromophores, were developed for use in dye-sensitised solar cells (DSSCs). These coumarin dyes have been used to fabricate DSSCs using I-/I-3(-) liquid electrolytes and their device performances were compared with that of NKX-2677 as a standard dye. Even though HKK-CM2 and HKK-CM3 have more extended aromatic units than HKK-CM1, the degree of pi-conjugation in HKK-CM2 and HKK-CM3 is less efficient than that of HKK-CM1, due to the relatively larger torsion angle between the plane of the donor and that of the acceptor. It is also in a good agreement with Density Functional Theory (DFT) calculations. As a result, a solar cell based on HKK-CM1 sensitiser shows better photovoltaic performance with J(SC) 0114.2 mA cm(-2), V-OC of 0.60 V, and a fill factor of 0.70, corresponding to an overall conversion efficiency eta of 6.07% under the standard AM 1.5 irradiation, than HKK-CM2 and HKK-CM3-based solar cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.01.009