5,5''-dibromo-3'-bromomethyl-[2,2',5',2'']-terthiophene | 1352127-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5''-dibromo-3'-bromomethyl-[2,2',5',2'']-terthiophene
• CAS: 1352127-16-2
• 化学式: C₁₃H₇Br₃S₃
• 分子量: 499.109
• InChiKey: IDDPGFVZJXGMRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,5''-dibromo-3'-bromomethyl-[2,2',5',2'']-terthiophene 、 亚磷酸三乙酯 反应 3.0h， 以90%的产率得到5,5''-dibromo-3'-diethoxyphosphorylmethyl-[2,2',5',2'']-terthiophene
  参考文献：
  名称：

  Conjugated Side-Chain Isolated Polythiophene: Synthesis and Photovoltaic Application

  摘要：

  A design concept of "side chain isolation" was proposed for developing new polythiophene derivatives with conjugated side chain (CSC-PTs), and PTSTPA with styryl triphenylamine (TPA) side chain and unsubstituted tetrathienyl spacer was designed and synthesized. Compared to previously reported CSC-PTs, side chain isolated PT5TPA showed red shifted and enhanced pi-pi* transition absorption of the polymer backbone along with the shoulder peak and steep absorption edge, indicating improved planarity of the backbone. In addition, the unsubstituted thiophene spacer along the polymer backbone of the side chain isolated PTSTPA results in a lower HOMO energy level of the polymer at 5.1 eV. The polymer solar cell based on PT5TPA as donor and indene-C-60 bisadduct as acceptor displayed a power conversion efficiency of 3.6% with a high open circuit voltage of 0.94 V, under the illumination of AM1.5G, 100 mW/cm(2). The results indicate that the side chain isolated CSC-PTs could open a new way for developing high performance photovoltaic polymers.

  DOI：

  10.1021/ma201718x
• 作为产物：
  描述：

  5,5''-dibromo-3'-methyl-[2,2',5',2'']-terthiophene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 5,5''-dibromo-3'-bromomethyl-[2,2',5',2'']-terthiophene
  参考文献：
  名称：

  Conjugated Side-Chain Isolated Polythiophene: Synthesis and Photovoltaic Application

  摘要：

  A design concept of "side chain isolation" was proposed for developing new polythiophene derivatives with conjugated side chain (CSC-PTs), and PTSTPA with styryl triphenylamine (TPA) side chain and unsubstituted tetrathienyl spacer was designed and synthesized. Compared to previously reported CSC-PTs, side chain isolated PT5TPA showed red shifted and enhanced pi-pi* transition absorption of the polymer backbone along with the shoulder peak and steep absorption edge, indicating improved planarity of the backbone. In addition, the unsubstituted thiophene spacer along the polymer backbone of the side chain isolated PTSTPA results in a lower HOMO energy level of the polymer at 5.1 eV. The polymer solar cell based on PT5TPA as donor and indene-C-60 bisadduct as acceptor displayed a power conversion efficiency of 3.6% with a high open circuit voltage of 0.94 V, under the illumination of AM1.5G, 100 mW/cm(2). The results indicate that the side chain isolated CSC-PTs could open a new way for developing high performance photovoltaic polymers.

  DOI：

  10.1021/ma201718x