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 | 1259015-16-1

• 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[(2,5-bis(5'-hexyl-2,2'-bithiophene)thiophen-3-yl)]perylene-3,4,9,10-tetracarboxylic acid diimide
• 英文别名: 11-[2,5-Bis[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-3-yl]-7,18-bis(2-ethylhexyl)-22-[5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-2-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-3-yl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone；11-[2,5-bis[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-3-yl]-7,18-bis(2-ethylhexyl)-22-[5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-2-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-3-yl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 1259015-16-1
• 化学式: C₁₀₄H₁₁₀N₂O₄S₁₀
• 分子量: 1772.69
• InChiKey: CPZVJDKDJGJKBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  29.7
• 重原子数：
  120
• 可旋转键数：
  42
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  275
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  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

文献信息

• Low Band Gap Thiophene−Perylene Diimide Systems with Tunable Charge Transport Properties
  作者：Ganapathy Balaji、Tejaswini S. Kale、Ashok Keerthi、Andrea M. Della Pelle、S. Thayumanavan、Suresh Valiyaveettil

  DOI：10.1021/ol1023486

  日期：2011.1.7

  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.