2,5-bis(2-ethylhexyl)-3,6-bis(5-(2-naphthyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H, 5H)-dione | 1401102-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,5-bis(2-ethylhexyl)-3,6-bis(5-(2-naphthyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H, 5H)-dione
• 英文别名: 2,5-Bis(2-ethylhexyl)-1,4-bis(5-naphthalen-2-ylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1401102-55-3
• 化学式: C₅₀H₅₂N₂O₂S₂
• 分子量: 777.107
• InChiKey: GZCJRLRBHAEURV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,6-双(5-溴-2-噻吩基)-2,5-双(2-乙基己基)-2,5-二氢吡咯并[3,4-C]吡咯-1,4-二酮 、 2-萘硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以89%的产率得到2,5-bis(2-ethylhexyl)-3,6-bis(5-(2-naphthyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H, 5H)-dione
  参考文献：
  名称：

  A solution-processable diketopyrrolopyrrole dye molecule with (fluoronaphthyl)thienyl endgroups for organic solar cells

  摘要：

  A solution-processable dye molecule DPP(TFNa)(2) that consists of diketopyrrolopyrrole (DPP) as the core and 5-(6-fluoro-2-naphthyl)thienyl as the endgroups is presented for bulk heterojunction organic solar cells. DPP(TFNa)(2) is a crystalline solid with a T-m, of approximately 216 degrees C. X-ray diffraction experiments reveal that thermal annealing increases crystallinity of the as-cast film, thus beneficial to the absorption and charge-transport properties. DPP(TFNa)(2) exhibits two reversible one-electron oxidation waves at 0.87 and 1.16 V vs. Ag/AgCl reference electrode, respectively. Fitting the space-charge-limited current characteristics in a hole-only device results in a hole mobility of similar to 2.7 x 10(-4) cm(2) V-1 s(-1) at low voltages for DPP(TFNa)(2). A preliminary characterization of the solar cell (ITO/PEDOT:PSS/DPP(TFNa)(2):PC61BM/AI) yields a power conversion efficiency of approximately 3.0% under simulated AM 1.5G illumination (66.4 and 100 mW cm(-2), respectively). The fluorine effects on material properties such as morphology, absorption, electrochemistry, charge transport and the resulting device performance are discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.09.022

文献信息

• Diketopyrrolopyrrole based highly crystalline conjugated molecules for application in small molecule donor-polymer acceptor nonfullerene organic solar cells
  作者：Jianyu Yuan、Wanli Ma

  DOI：10.1016/j.orgel.2016.10.021

  日期：2016.12

  In order to specifically investigate the low efficiency of small molecule donor-polymer acceptor (M-P) nonfullerene organic solar cells, we have successfully modify the synthesis of a series of D-π-A-π-D conjugated molecules containing diketopyrrolopyrrole (DPP) and different end groups. By incorporation of end group with different size of π-conjugation (benzene, naphthalene and pyrene), we further

  为了具体研究小分子供体-聚合物受体（MP）非富勒烯有机太阳能电池的低效率，我们成功地修饰了一系列包含二酮吡咯并吡咯（DPP）和D-π-A-π-D共轭分子的合成不同的端组。通过结合具有不同π共轭尺寸的端基（苯，萘和pyr），我们进一步提高了填充因子（FF）和短电流密度（J sc）供体分子。我们的实验结果和理论计算证明，端基的大小可以通过改变分子的共面性来影响分子的结晶度，迁移率和分子间堆积。由于改善了结晶度，形态和微调的迁移率，我们证明了FF的增加，约4.5 mA / cm 2的高J sc和2.05％的功率转换效率，这是MP富勒烯报道的最高效率之一太阳能电池。我们的结果为将来实现更高性能的MP非富勒烯太阳能电池提供了机遇和可能性。