2,3,9,10-tetracyano-6,13-bis-(triisopropylsilylethynyl)pentacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 并五苯
• 英文名称: 2,3,9,10-tetracyano-6,13-bis-(triisopropylsilylethynyl)pentacene
• 英文别名: 2,3,9,10-CN4-TIPS-Pn；2,3,9,10-Tetracyano-6,13-bis(triisopropylsilylethynyl) pentacene；6,13-bis[2-tri(propan-2-yl)silylethynyl]pentacene-2,3,9,10-tetracarbonitrile
• 化学式: C₄₈H₅₀N₄Si₂
• 分子量: 739.123
• InChiKey: RJCUGPOWXUXDEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.93
• 重原子数：
  54
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 四(三苯基膦)钯 tin(ll) chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.3h， 生成 2,3,9,10-tetracyano-6,13-bis-(triisopropylsilylethynyl)pentacene
  参考文献：
  名称：

  Synthesis and Characterization of Electron-Deficient Pentacenes

  摘要：

  Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the pi-stacking in these systems. The halogenated pentacene derivatives described here (X = Br, X' = H, and X = X' = F) are all stable and soluble, with reduction potentials significantly lower than that of the parent functionalized pentacene (X = X' = H). The bromopentacenes could be further elucidated to pentacene nitriles, further decreasing the acene's reduction potential, while the charge-carrier mobility in the fluorinated systems was shown to scale with the degree of fluorine substitution.

  DOI：

  10.1021/ol050872b

文献信息

• Soluble n-type pentacene derivatives as novel acceptors for organic solar cells
  作者：Yee-Fun Lim、Ying Shu、Sean R. Parkin、John E. Anthony、George G. Malliaras

  DOI：10.1039/b818693f

  日期：——

  6,13-Bis(triisopropylsilylethynyl) (TIPS)-pentacene has proven to be a promising soluble p-type material for organic thin film transistors as well as for photovoltaics. In this work, we show that adding electron-withdrawing nitrile functional groups to TIPS-pentacene turns it into an n-type material, which can be used as an acceptor for organic solar cells. Several new cyanopentacenes with different trialkylsilyl functional groups have been synthesized. The HOMO–LUMO energy levels can be tuned by varying the number of nitrile groups, while the trialkylsilyl groups control crystal packing and film morphology. Solar cells were fabricated from a blend of poly(3-hexylthiophene) (P3HT) as the donor and the cyanopentacenes as acceptors, and we found that the acceptors that stack in a 1D “sandwich-herringbone” exhibited the best performance of derivatives in this study. A solar cell fabricated from a blend of P3HT and 2,3-dicyano-6,13-bis-(tricyclopentylsilylethynyl)pentacene (2,3-CN2-TCPS-Pn) exhibited a power conversion efficiency of 0.43% under 100 mW cm−2AM 1.5 illumination.

  6,13-双（三异丙基硅基乙炔基）(TIPS)-五聚烯已经被证明是一种有前景的可溶性p型材料，适用于有机薄膜晶体管和光伏材料。在本研究中，我们展示了通过向TIPS-五聚烯中添加强电子吸引的氰基功能团，可以将其转变为n型材料，进而作为有机太阳能电池的受体。我们合成了几种不同三烷基硅基功能团的新氰基五聚烯。通过改变氰基数量可以调节HOMO-LUMO能级，而三烷基硅基团则控制晶体堆积和薄膜形态。我们用聚（3-己基噻吩）（P3HT）作为供体，与氰基五聚烯混合制成太阳能电池，发现以1D“夹心人字形”堆叠的受体在该研究中表现出最佳性能。由P3HT和2,3-二氰基-6,13-双（三环戊基硅基乙炔基）五聚烯（2,3-CN2-TCPS-Pn）混合制成的太阳能电池在100 mW cm−2 AM 1.5照明下展现出0.43%的光电转换效率。