N,N'-di(2-ethylhexyl)-1,7-di(2,5dibromothiophen-3-yl)perylene-3,4,9,10-tetracarboxylic acid diimide | 1259015-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-di(2-ethylhexyl)-1,7-di(2,5dibromothiophen-3-yl)perylene-3,4,9,10-tetracarboxylic acid diimide
• CAS: 1259015-19-4
• 化学式: C₄₈H₄₂Br₄N₂O₄S₂
• 分子量: 1094.62
• InChiKey: IBQVQHOBLJZKBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.87
• 重原子数：
  60.0
• 可旋转键数：
  14.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5’-己基-2,2’-联噻吩-5-硼酸频哪醇酯 、 N,N'-di(2-ethylhexyl)-1,7-di(2,5dibromothiophen-3-yl)perylene-3,4,9,10-tetracarboxylic acid diimide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以78%的产率得到N,N'-di(2-ethylhexyl)-1,7-di[(2,5-bis(5'-hexyl-2,2'-bithiophene)thiophen-3-yl)]perylene-3,4,9,10-tetracarboxylic acid diimide
  参考文献：
  名称：

  Low Band Gap Thiophene−Perylene Diimide Systems with Tunable Charge Transport Properties

  摘要：

  Perylenediimide-pentathiophene systems with varied architecture of thiophene units were synthesized. The photophysical, electrochemical, and charge transport behavior of the synthesized compounds were studied. Both molecules showed a low band gap of similar to 1.4 eV. Surprisingly, the molecule with pentathiophene attached via beta-position to the PDI unit upon annealing showed a predominant hole mobility of 1 x 10(-4) cm(2) V-1 s(-1) whereas the compound with branched pentathiophene attached via beta-position showed an electron mobility of 9.8 x 10(-7) cm(2) V-1 s(-1). This suggests that charge transport properties can be tuned by simply varying the architecture of pentathiophene units.

  DOI：

  10.1021/ol1023486
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 四(三苯基膦)钯 、 硫酸 、 溴 、 potassium carbonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 氯仿 、 水 为溶剂， 反应 28.0h， 生成 N,N'-di(2-ethylhexyl)-1,7-di(2,5dibromothiophen-3-yl)perylene-3,4,9,10-tetracarboxylic acid diimide
  参考文献：
  名称：

  Low Band Gap Thiophene−Perylene Diimide Systems with Tunable Charge Transport Properties

  摘要：

  Perylenediimide-pentathiophene systems with varied architecture of thiophene units were synthesized. The photophysical, electrochemical, and charge transport behavior of the synthesized compounds were studied. Both molecules showed a low band gap of similar to 1.4 eV. Surprisingly, the molecule with pentathiophene attached via beta-position to the PDI unit upon annealing showed a predominant hole mobility of 1 x 10(-4) cm(2) V-1 s(-1) whereas the compound with branched pentathiophene attached via beta-position showed an electron mobility of 9.8 x 10(-7) cm(2) V-1 s(-1). This suggests that charge transport properties can be tuned by simply varying the architecture of pentathiophene units.

  DOI：

  10.1021/ol1023486