di-tert-butyl 2,2'-(benzo[d][2,1,3]thiadiazole-4,7-diyl)bis(thiophene-3-carboxylate) | 1268883-80-2

• 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: di-tert-butyl 2,2'-(benzo[d][2,1,3]thiadiazole-4,7-diyl)bis(thiophene-3-carboxylate)
• CAS: 1268883-80-2
• 化学式: C₂₄H₂₄N₂O₄S₃
• 分子量: 500.664
• InChiKey: OXSINMVLFHKGST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.38
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 2,2'-(benzo[d][2,1,3]thiadiazole-4,7-diyl)bis(thiophene-3-carboxylate) 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 以83%的产率得到di-tert-butyl 2,2'-(benzo[d][2,1,3]thiadiazole-4,7-diyl)bis(5-iodothiophene-3-carboxylate)
  参考文献：
  名称：

  Low-Bandgap Donor−Acceptor Conjugated Polymer Sensitizers for Dye-Sensitized Solar Cells

  摘要：

  A set of two donor acceptor-type conjugated polymers with carboxylic acid side groups have been synthesized and utilized as active materials for dye-sensitized solar cells (DSSCs). The polymers feature a pi-conjugated backbone consisting of an electron-poor 2,1,3-benzothiadiazole (BTD, acceptor) unit, alternating with either a thiophene-fluorene-thiophene triad (2a) or a terthiophene (3a) segment as the donor. The donor-acceptor polymers absorb broadly throughout the visible region, with terthiophene-BTD polymer 3a exhibiting an absorption onset at approximately 625 nm corresponding to a similar to 1.9 eV bandgap. The polymers adsorb onto the surface of nanostructured TiO2 due to interaction of the polar carboxylic acid units with the metal oxide surface. The resulting films absorb visible light strongly, and their spectra approximately mirror the polymers' solution absorption. Interestingly, a series of samples of 3a with different molecular weight (M-n) adsorb to TiO2 to an extent that varies inversely with M-n. DSSCs that utilize the donor acceptor polymers as sensitizers were tested using an I-/I-3(-) electrolyte. Importantly, for the set of polymer sensitizers 3a with varying M, the DSSC efficiency varies inversely with NI, a result that reflects the difference in adsorption efficiency observed in the film absorption experiments. The best DSSC cell tested is based on a sample of 3a with M-n similar to 4000, and it exhibits a similar to 65% peak IPCE with J(sc) similar to 12.6 mA cm-2 under AM 1.5 illumination and an overall power conversion efficiency of similar to 3%.

  DOI：

  10.1021/ja109926k
• 作为产物：
  描述：

  3-噻吩甲酸甲酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 di-tert-butyl 2,2'-(benzo[d][2,1,3]thiadiazole-4,7-diyl)bis(thiophene-3-carboxylate)
  参考文献：
  名称：

  Low-Bandgap Donor−Acceptor Conjugated Polymer Sensitizers for Dye-Sensitized Solar Cells

  摘要：

  A set of two donor acceptor-type conjugated polymers with carboxylic acid side groups have been synthesized and utilized as active materials for dye-sensitized solar cells (DSSCs). The polymers feature a pi-conjugated backbone consisting of an electron-poor 2,1,3-benzothiadiazole (BTD, acceptor) unit, alternating with either a thiophene-fluorene-thiophene triad (2a) or a terthiophene (3a) segment as the donor. The donor-acceptor polymers absorb broadly throughout the visible region, with terthiophene-BTD polymer 3a exhibiting an absorption onset at approximately 625 nm corresponding to a similar to 1.9 eV bandgap. The polymers adsorb onto the surface of nanostructured TiO2 due to interaction of the polar carboxylic acid units with the metal oxide surface. The resulting films absorb visible light strongly, and their spectra approximately mirror the polymers' solution absorption. Interestingly, a series of samples of 3a with different molecular weight (M-n) adsorb to TiO2 to an extent that varies inversely with M-n. DSSCs that utilize the donor acceptor polymers as sensitizers were tested using an I-/I-3(-) electrolyte. Importantly, for the set of polymer sensitizers 3a with varying M, the DSSC efficiency varies inversely with NI, a result that reflects the difference in adsorption efficiency observed in the film absorption experiments. The best DSSC cell tested is based on a sample of 3a with M-n similar to 4000, and it exhibits a similar to 65% peak IPCE with J(sc) similar to 12.6 mA cm-2 under AM 1.5 illumination and an overall power conversion efficiency of similar to 3%.

  DOI：

  10.1021/ja109926k

文献信息

• Organic Chromophores Designed for Hole Injection into Wide-Band-Gap Metal Oxides for Solar Fuel Applications
  作者：Linda Nhon、Aaron D. Taggart、Taylor Moot、M. Kyle Brennaman、Pradeepkumar Jagadesan、Kirk S. Schanze、James F. Cahoon、John R. Reynolds

  DOI：10.1021/acs.chemmater.0c01477

  日期：2020.10.13

  ∼−6.50 eV. The absorption profiles for these chromophores span throughout the visible region. The new chromophore reported here, benzobis(thiadiazole)bis(thiophene-3-carboxylic acid), T2-BBT, adsorbed onto PbTiO3, obtained a maximum absorbed photon-to-current conversion efficiency of 54%. These results highlight the importance of designing chromophores with favorable redox potentials to study promising

  串联染料敏化的光电合成电池的功率转换效率受到可用于光电阴极的p型金属氧化物半导体和生色团的数量的限制。在这里，我们介绍了一种新型的供体-受体-供体有机发色团，它们具有最高的最高占据分子轨道（HOMO）水平，旨在将空穴注入PbTiO 3中，后者是NiO的宽带隙金属氧化物的替代物。电化学测量表明，我们可以将发色团的电子亲和力范围调节在约4.30和3.30 eV之间，并将电离电势保持在约-6.50 eV。这些生色团的吸收曲线跨越了整个可见光区域。此处报道了新的生色团，吸附在PbTiO 3上的苯并双（噻二唑）双（噻吩-3-羧酸）T2-BBT，获得的最大吸收光子至电流转换效率为54％。这些结果突出了设计具有良好氧化还原电势的生色团以研究用于光阴极应用的有前途的p型宽带隙金属氧化物的重要性。