5,6-bis(4-ethyloctyl)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole | 1207196-52-8

• 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: 5,6-bis(4-ethyloctyl)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole
• CAS: 1207196-52-8
• 化学式: C₃₄H₄₈N₂S₃
• 分子量: 580.967
• InChiKey: SUANQZROMPPNME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.23
• 重原子数：
  39.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,6-bis(4-ethyloctyl)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 生成 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(4-ethyloctyl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Donor−Acceptor Polymers Incorporating Alkylated Dithienylbenzothiadiazole for Bulk Heterojunction Solar Cells: Pronounced Effect of Positioning Alkyl Chains

  摘要：

  4,7-Di(thiophen-2-yl)benzothiadiazole (DTBT) has been used to construct a number of donor-acceptor low band gap polymers for bulk heterojunction (BHJ) photovoltaics with high efficiency numbers. Its strong tendency to pi-stack often leads to polymers with low molecular weight and poor solubility, which could potentially be alleviated by anchoring solubilizing chains onto the DTBT unit. A systematic study of the effect of positioning alkyl chains on DTBT on properties of polymers was implemented by investigating a small library of structurally related polymers with identical Conjugated backbone. This series of donor-acceptor polymers employed a common donor unit, benzo[2,1-b:3,4-b']dithiophene (BDT). and modified DTBT as the acceptor unit. Three variations of modified DTBT units Were prepared with alkyl side chains at (a) the 5- and 6-positions of 2,1,3-benzothiadiazole (DTsolBT), (b) 3-positions of the flanking thienyl groups (3DTBT), and (c) 4-positions (4DTBT), in addition to the unmodified DTBT. Contrary to results from previous studies, optical and electrochemical studies disclosed almost identical band gap and energy levels between PBDT-4DTBT and PBDT-DTBT. These results indicated that anchoring solubilizing alkyl chains on the 4-positions of DTBT only introduced a minimum steric hindrance within BDT-DTBT maintaining the extended conjugation of the fundamental structural unit (BDT-DTBT). More importantly, the additional high molecular weight and excellent solubility of PBDT-4DTBT led to a more uniform mixture with PCBM, with better control on the film morphology. All these features of PBDT-4DTBT led to a significantly improved efficiency of related BHJ solar cells (up to 2.2% has beep, observed), triple the efficiency obtained from BHJ devices fabricated from the "conventional" PBDT-DTBT (0.72%). Our discovery reinforced the importance of high molecular weight and good solubility of donor polymers for BHJ solar cells, in addition to a low band gap and a low HOMO energy level, in order to further enhance the device efficiencies.

  DOI：

  10.1021/ma902241b
• 作为产物：
  描述：

  1,2-二溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 氯化亚砜 、 sodium iodate 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 碘 、 硝酸 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 5,6-bis(4-ethyloctyl)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Donor−Acceptor Polymers Incorporating Alkylated Dithienylbenzothiadiazole for Bulk Heterojunction Solar Cells: Pronounced Effect of Positioning Alkyl Chains

  摘要：

  4,7-Di(thiophen-2-yl)benzothiadiazole (DTBT) has been used to construct a number of donor-acceptor low band gap polymers for bulk heterojunction (BHJ) photovoltaics with high efficiency numbers. Its strong tendency to pi-stack often leads to polymers with low molecular weight and poor solubility, which could potentially be alleviated by anchoring solubilizing chains onto the DTBT unit. A systematic study of the effect of positioning alkyl chains on DTBT on properties of polymers was implemented by investigating a small library of structurally related polymers with identical Conjugated backbone. This series of donor-acceptor polymers employed a common donor unit, benzo[2,1-b:3,4-b']dithiophene (BDT). and modified DTBT as the acceptor unit. Three variations of modified DTBT units Were prepared with alkyl side chains at (a) the 5- and 6-positions of 2,1,3-benzothiadiazole (DTsolBT), (b) 3-positions of the flanking thienyl groups (3DTBT), and (c) 4-positions (4DTBT), in addition to the unmodified DTBT. Contrary to results from previous studies, optical and electrochemical studies disclosed almost identical band gap and energy levels between PBDT-4DTBT and PBDT-DTBT. These results indicated that anchoring solubilizing alkyl chains on the 4-positions of DTBT only introduced a minimum steric hindrance within BDT-DTBT maintaining the extended conjugation of the fundamental structural unit (BDT-DTBT). More importantly, the additional high molecular weight and excellent solubility of PBDT-4DTBT led to a more uniform mixture with PCBM, with better control on the film morphology. All these features of PBDT-4DTBT led to a significantly improved efficiency of related BHJ solar cells (up to 2.2% has beep, observed), triple the efficiency obtained from BHJ devices fabricated from the "conventional" PBDT-DTBT (0.72%). Our discovery reinforced the importance of high molecular weight and good solubility of donor polymers for BHJ solar cells, in addition to a low band gap and a low HOMO energy level, in order to further enhance the device efficiencies.

  DOI：

  10.1021/ma902241b