N,N’-bis-n-octyl-2,5,8,11-tetra-phenethyl-3,4,9,10-perylenediimide | 1207954-40-2

• 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’-bis-n-octyl-2,5,8,11-tetra-phenethyl-3,4,9,10-perylenediimide
• 英文别名: 7,18-Dioctyl-10,15,21,25-tetrakis(2-phenylethyl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 1207954-40-2
• 化学式: C₇₂H₇₄N₂O₄
• 分子量: 1031.39
• InChiKey: KNOWTXXEAGRTCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.4
• 重原子数：
  78
• 可旋转键数：
  26
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙烯 、 N,N'-二正辛烷基-3,4,9,10-苝四甲酰二亚胺 在 RuH₂(CO)(PPh₃)₃ 作用下， 以 均三甲苯 为溶剂， 反应 48.0h， 以78%的产率得到N,N’-bis-n-octyl-2,5,8,11-tetra-phenethyl-3,4,9,10-perylenediimide
  参考文献：
  名称：

  Slip-Stacked Perylenediimides as an Alternative Strategy for High Efficiency Nonfullerene Acceptors in Organic Photovoltaics

  摘要：

  Perylenediimide (PDI)-based acceptors offer a potential replacement for fullerenes in bulk-heterojunction (BHJ) organic photovoltaic cells (OPVs). The most promising efforts have focused on creating twisted PDI dimers to disrupt aggregation and thereby suppress excimer formation. Here, we present an alternative strategy for developing high-performance OPVs based on PDI acceptors that promote slip-stacking in the solid state, thus preventing the coupling necessary for rapid excimer formation. This packing structure is accomplished by substitution at the PDI 2,5,8,11-positions ("headland positions"). Using this design principle, three PDI acceptors, N,N-bis(nocty1)-2,5,8,11-tetra(n-hexyl)-PDI (Hexyl-PDI), N,N-bis(n-octyl)-2,5,8,11-tetraphenethyl-PDI (Phenethyl-PDI), and N,N-bis(n-octyl)-2,5,8,11-tetraphenyl-PDI (Phenyl-PDI), were synthesized, and their molecular and electronic structures were characterized. They were then blended with the donor polymer PBTI3T, and inverted OPVs of the structure ITO/ZnO/Active Layer/MoO3/Ag were fabricated and characterized. Of these, 1:1 PBTI3T:Phenyl-PDI proved to have the best performance with J(sc) = 6.56 mA/cm(2), V-oc = 1.024 V, FF = 54.59%, and power conversion efficiency (PCE) = 3.67%. Devices fabricated with Phenethyl-PDI and Hexyl-PDI have significantly lower performance. The thin film morphology and the electronic and photophysical properties of the three materials are examined, and although all three materials undergo efficient charge separation, PBTI3T:Phenyl-PDI is found to have the deepest LUMO, intermediate crystallinity, and the most well-mixed domains. This minimizes geminate recombination in Phenyl-PDI OPVs and affords the highest PCE. Thus, slip-stacked PDI strategies represent a promising approach to fullerene replacements in BHJ OPVs.

  DOI：

  10.1021/ja508814z

文献信息

• Photophysics and Redox Properties of Rylene Imide and Diimide Dyes Alkylated Ortho to the Imide Groups
  作者：Joseph E. Bullock、Michael T. Vagnini、Charusheela Ramanan、Dick T. Co、Thea M. Wilson、Jay W. Dicke、Tobin J. Marks、Michael R. Wasielewski

  DOI：10.1021/jp908679c

  日期：2010.2.11

  naphthalene-1,4:5,8-bis(dicarboximide) (NI), perylene-3,4-dicarboximide (PMI), perylene-3,4:9,10-bis(dicarboximide) (PDI), and terrylene-3,4:11,12-bis(dicarboximide) (TDI). The monoimides were dialkylated, while the diimides were tetraalkylated, with the exception of NI, which could only be dialkylated due to steric hindrance. The absorption, fluorescence, transient absorption spectra, and lowest excited

  钌催化的CH键活化可直接将源自苯乙烯的苯乙基直接连接到各种萘嵌苯二酰亚胺和二酰亚胺中的邻苯二甲酰亚胺位置，包括萘1,8-双二甲酰亚胺（NMI），萘1,4 ：5,8-双（二​​甲酰亚胺）（NI）、,-3,4-二甲酰亚胺（PMI），per-3,4：9,10-双（二甲酰亚胺）（PDI）和三甲苯-3,4：11 ，12-双（二甲叉酰亚胺）（TDI）。除NI外，单酰亚胺是二烷基化的，而二酰亚胺是四烷基化的，NI由于空间位阻而只能被二烷基化。这些发色团的吸收，荧光，瞬态吸收光谱和最低激发单重态寿命（除NI外）与未取代的母发色团几乎相同。二烷基化生色团的还原电势比母体化合物高约100 mV负电势，氧化电势比母体化合物的正电势低约40 mV正电，而四烷基化化合物的相应电势比负电基体强约200 mV，正电势低约100 mV。它们的母体化合物的那些。PDI自由基阴离子的连续波电子顺磁共振（EPR）和电子核双共振
• Selectively Functionalized Rylene Imides and Diimides
  申请人：Wasielewski Michael R.

  公开号：US20110079773A1

  公开（公告）日：2011-04-07

  Disclosed are new selectively functionalized rylene imides and diimides that can exhibit desirable electronic properties and can possess processing advantages including solution-processability and/or good stability at ambient conditions.
• Slip-Stacked Perylenediimides as an Alternative Strategy for High Efficiency Nonfullerene Acceptors in Organic Photovoltaics
  作者：Patrick E. Hartnett、Amod Timalsina、H. S. S. Ramakrishna Matte、Nanjia Zhou、Xugang Guo、Wei Zhao、Antonio Facchetti、Robert P. H. Chang、Mark C. Hersam、Michael R. Wasielewski、Tobin J. Marks

  DOI：10.1021/ja508814z

  日期：2014.11.19

  Perylenediimide (PDI)-based acceptors offer a potential replacement for fullerenes in bulk-heterojunction (BHJ) organic photovoltaic cells (OPVs). The most promising efforts have focused on creating twisted PDI dimers to disrupt aggregation and thereby suppress excimer formation. Here, we present an alternative strategy for developing high-performance OPVs based on PDI acceptors that promote slip-stacking in the solid state, thus preventing the coupling necessary for rapid excimer formation. This packing structure is accomplished by substitution at the PDI 2,5,8,11-positions ("headland positions"). Using this design principle, three PDI acceptors, N,N-bis(nocty1)-2,5,8,11-tetra(n-hexyl)-PDI (Hexyl-PDI), N,N-bis(n-octyl)-2,5,8,11-tetraphenethyl-PDI (Phenethyl-PDI), and N,N-bis(n-octyl)-2,5,8,11-tetraphenyl-PDI (Phenyl-PDI), were synthesized, and their molecular and electronic structures were characterized. They were then blended with the donor polymer PBTI3T, and inverted OPVs of the structure ITO/ZnO/Active Layer/MoO3/Ag were fabricated and characterized. Of these, 1:1 PBTI3T:Phenyl-PDI proved to have the best performance with J(sc) = 6.56 mA/cm(2), V-oc = 1.024 V, FF = 54.59%, and power conversion efficiency (PCE) = 3.67%. Devices fabricated with Phenethyl-PDI and Hexyl-PDI have significantly lower performance. The thin film morphology and the electronic and photophysical properties of the three materials are examined, and although all three materials undergo efficient charge separation, PBTI3T:Phenyl-PDI is found to have the deepest LUMO, intermediate crystallinity, and the most well-mixed domains. This minimizes geminate recombination in Phenyl-PDI OPVs and affords the highest PCE. Thus, slip-stacked PDI strategies represent a promising approach to fullerene replacements in BHJ OPVs.