5,8-bis(5-bromo-2-thienyl)pyrido[3,4-b]pyrazine | 1007128-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 英文名称: 5,8-bis(5-bromo-2-thienyl)pyrido[3,4-b]pyrazine
• 英文别名: 5,8-Bis(5-bromothiophen-2-yl)pyrido[3,4-b]pyrazine；5,8-bis(5-bromothiophen-2-yl)pyrido[3,4-b]pyrazine
• CAS: 1007128-61-1
• 化学式: C₁₅H₇Br₂N₃S₂
• 分子量: 453.181
• InChiKey: NNHNVZDVUCQYDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,8-dithienylpyrido[3,4-b]pyrazine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 邻二氯苯 为溶剂， 反应 3.0h， 以66%的产率得到5,8-bis(5-bromo-2-thienyl)pyrido[3,4-b]pyrazine
  参考文献：
  名称：

  Toward a Rational Design of Poly(2,7-Carbazole) Derivatives for Solar Cells

  摘要：

  On the basis of theoretical models and calculations, several alternating polymeric structures have been investigated to develop optimized poly(2,7-carbazole) derivatives for solar cell applications. Selected low band gap alternating copolymers have been obtained via a Suzuki coupling reaction. A good correlation between DFT theoretical calculations performed on model compounds and the experimental HOMO, LUMO, and band gap energies of the corresponding polymers has been obtained. This study reveals that the alternating copolymer HOMO energy level is mainly fixed by the carbazole moiety, whereas the LUMO energy level is mainly related to the nature of the electron-withdrawing comonomer. However, solar cell performances are not solely driven by the energy levels of the materials. Clearly, the molecular weight and the overall organization of the polymers are other important key parameters to consider when developing new polymers for solar cells. Preliminary measurements have revealed hole mobilities of about 1 x 10(-3) cm(2).V-1.s(-1) and a power conversion efficiency (PCE) up to 3.6%. Further improvements are anticipated through a rational design of new symmetric low band gap poly(2,7-carbazole) derivatives.

  DOI：

  10.1021/ja0771989

文献信息

• Toward a Rational Design of Poly(2,7-Carbazole) Derivatives for Solar Cells
  作者：Nicolas Blouin、Alexandre Michaud、David Gendron、Salem Wakim、Emily Blair、Rodica Neagu-Plesu、Michel Belletête、Gilles Durocher、Ye Tao、Mario Leclerc

  DOI：10.1021/ja0771989

  日期：2008.1.1

  On the basis of theoretical models and calculations, several alternating polymeric structures have been investigated to develop optimized poly(2,7-carbazole) derivatives for solar cell applications. Selected low band gap alternating copolymers have been obtained via a Suzuki coupling reaction. A good correlation between DFT theoretical calculations performed on model compounds and the experimental HOMO, LUMO, and band gap energies of the corresponding polymers has been obtained. This study reveals that the alternating copolymer HOMO energy level is mainly fixed by the carbazole moiety, whereas the LUMO energy level is mainly related to the nature of the electron-withdrawing comonomer. However, solar cell performances are not solely driven by the energy levels of the materials. Clearly, the molecular weight and the overall organization of the polymers are other important key parameters to consider when developing new polymers for solar cells. Preliminary measurements have revealed hole mobilities of about 1 x 10(-3) cm(2).V-1.s(-1) and a power conversion efficiency (PCE) up to 3.6%. Further improvements are anticipated through a rational design of new symmetric low band gap poly(2,7-carbazole) derivatives.