N,N'-Bis(n-octyl)pyrromellitimide | 6626-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N,N'-Bis(n-octyl)pyrromellitimide
• 英文别名: 2,6-dioctylpyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone；N,N'-di(n-octyl)pyromellitic diimide；2,6-Dioctylpyrrolo[3,4-f]isoindole-1,3,5,7(2h,6h)-tetrone；2,6-dioctylpyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• CAS: 6626-71-7
• 化学式: C₂₆H₃₆N₂O₄
• 分子量: 440.583
• InChiKey: RFZVMUWVEMNLPS-UHFFFAOYSA-N

物化性质

• 沸点：
  572.7±33.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-Bis(n-octyl)pyrromellitimide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以63%的产率得到N,N'-di(n-octyl)pyromellitic diimide
  参考文献：
  名称：

  Pyromellitic dithioimides: thionation improves air-stability and electron mobility of N-type organic field-effect transistors

  摘要：

  二亚胺化合物的硫化不仅稳定了LUMO能级，还增强了电子迁移性和空气稳定性。

  DOI：

  10.1039/c5cc04674b
• 作为产物：
  描述：

  辛胺 、 均苯四甲酸二酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以76%的产率得到N,N'-Bis(n-octyl)pyrromellitimide
  参考文献：
  名称：

  Pyromellitic dithioimides: thionation improves air-stability and electron mobility of N-type organic field-effect transistors

  摘要：

  二亚胺化合物的硫化不仅稳定了LUMO能级，还增强了电子迁移性和空气稳定性。

  DOI：

  10.1039/c5cc04674b

文献信息

• Functionalized and Degradable Polyphthalaldehyde Derivatives
  作者：J. Patrick Lutz、Oleg Davydovich、Matthew D. Hannigan、Jeffrey S. Moore、Paul M. Zimmerman、Anne J. McNeil

  DOI：10.1021/jacs.9b07508

  日期：2019.9.18

  polyphthalaldehyde derivatives has not been systematically studied. Herein, we investigate the cationic polymerization of seven o-phthalaldehyde derivatives and demonstrate that judicious choice of substituent results in materials with a wide range of ceiling temperatures (<-60 to 106 °C) and decomposition temperatures (109-196 °C). We anticipate that these new polymers and their derivatives will enable researchers

  解聚回单体的聚合物可以反复进行化学回收，从而减少对环境的影响。聚苯二醛是一种亚稳态聚合物，由于其较低的上限温度，可以快速定量解聚。然而，取代对聚苯二醛衍生物理化性质的影响尚未得到系统研究。在此，我们研究了七种邻苯二甲醛衍生物的阳离子聚合，并证明明智地选择取代基会导致材料具有广泛的上限温度（<-60 至 106 °C）和分解温度（109-196 °C）。我们预计这些新聚合物及其衍生物将使研究人员能够获得具有可调热、物理和化学特性的可降解材料。
• One‐Pot Domino Carbonylation Protocol for Aromatic Diimides toward n‐Type Organic Semiconductors
  作者：Xiaolong Fu、Yonggang Zhen、Zhenjie Ni、Yang Li、Huanli Dong、Jay S. Siegel、Wenping Hu

  DOI：10.1002/anie.202003179

  日期：2020.8.10

  Aromatic diimides are one of the most important chromophores in the construction of n‐type organic semiconductors, which lag far behind their p‐type counterpart but are necessary for ambipolar transistors, p‐n junctions and organic complementary circuits. Herein, we establish a facile one‐pot domino synthetic protocol for aromatic diimides via palladium‐catalyzed carbonylation of tetrabromo aromatic

  芳香族二酰亚胺是n型有机半导体构造中最重要的生色团之一，其远远落后于其p型对应物，但对于双极晶体管，p-n结和有机互补电路必不可少。在这里，我们通过钯催化的四溴芳烃前体的羰基化反应，建立了一种用于芳族二酰亚胺的简便的一锅多米诺合成协议。以四溴环戊二烯（TBrCor）和四溴代2,7-二叔丁基py（TBrPy）为例，我们获得了二酰亚胺衍生物，产率约为50％，比传统的多步二酰亚胺化高一个数量级。 。如香兰素二酰亚胺所示，
• Facile, One-Step Synthesis of 5-Substituted Thieno[3,4-<i>c</i>]pyrrole-4,6-dione by Palladium-Catalyzed Carbonylative Amidation
  作者：Shinichiro Fuse、Ryota Takahashi、Takashi Takahashi

  DOI：10.1002/ejoc.201500273

  日期：2015.6

  Described herein is a facile, one-step synthesis of 5-substituted thieno[3,4-c]pyrrole-4,6-diones (TPDs) by a palladium-catalyzed carbonylative amidation of commercially available dibromoaryl compounds under mild conditions. TPDs are important structural components for organic electronics. Our optimal conditions afforded the desired 5-n-octyl-TPD in a 63 % yield in one step. This is a considerably

  本文描述的是在温和条件下，通过钯催化的市售二溴芳基化合物的羰基化酰胺化，轻松一步合成 5-取代的噻吩并 [3,4-c] 吡咯-4,6-二酮 (TPD)。TPD 是有机电子产品的重要结构部件。我们的最佳条件一步提供了所需的 5-n-辛基-TPD，产率为 63%。与最传统的方法（12-22% 中的 5 个步骤）相比，这是一个显着改进的过程。此外，该方法还应用于吡啶并吡咯二酮 (PPD) 和吡咯并异吲哚四酮 (PIT) 的合成，它们也是各种重要的结构成分。功能材料和生物活性化合物。开发的合成方法将是对材料和药物发现过程的宝贵帮助。
• Long‐Lived Charge‐Transfer State in Spiro Compact Electron Donor–Acceptor Dyads Based on Pyromellitimide‐Derived Rhodamine: Charge Transfer Dynamics and Electron Spin Polarization
  作者：Xi Chen、Andrey A. Sukhanov、Yuxin Yan、Damla Bese、Cagri Bese、Jianzhang Zhao、Violeta K. Voronkova、Antonio Barbon、Halime Gul Yaglioglu

  DOI：10.1002/anie.202203758

  日期：2022.8.15

  A novel fully rigid spiro electron donor–acceptor dyad is prepared by linking the electron donor and acceptor via a spiro quaternary carbon atom, thus the torsion between the electron donor and acceptor is completely inhibited. The dyad shows a long-lived 3CT state (2.6 μs) with a high energy level (ca. 2.61 eV), the electron spin multiplicity of the CT state was confirmed with time-resolved EPR spectra

  通过螺季碳原子连接电子供体和受体，制备了一种新型的全刚性螺电子供体-受体二元组，从而完全抑制了电子供体和受体之间的扭转。该二元组显示出具有高能级（约 2.61 eV）的长寿命3 CT 状态（2.6 μs），CT 状态的电子自旋多重性通过时间分辨 EPR 光谱得到证实。
• Competitive Electron Transfer from the S₂ and S₁ Excited States of Zinc <i>m</i><i>eso</i>-Tetraphenylporphyrin to a Covalently Bound Pyromellitimide:  Dependence on Donor−Acceptor Structure and Solvent
  作者：Ryan T. Hayes、Christopher J. Walsh、Michael R. Wasielewski

  DOI：10.1021/jp037176i

  日期：2004.4.1

  Zinc meso-tetraphenylporphyrin (ZnTPP) is known to have a relatively Slow S-2 --> S-1 internal conversion rate, (1-3 ps)(-1), so that electron transfer from S-2 to a nearby acceptor is possible. We have synthesized two zinc porphyrins in which a pyromellitimide (PI) acceptor is attached to the para position of a meso-phenyl group of the porphyrin (ZnTPP-PI) or to that of a beta-phenyl group of the porphyrin (ZnTPP-beta-PhPI). We report here on competitive electron transfer from the S-2 (excitation at 420 nm) and S-1 states (excitation at 550 nm) of these zinc porphyrins to PI in 2-methyltetrahydrofuran (MTHF) and toluene. Our transient absorption studies show that efficient electron transfer occurs from S-2 of ZnTPP to PI in these porphyrins despite the presence of the intervening phenyl between the zinc porphyrin macrocycle and the PI acceptor. Moreover, the results show that while charge separation from S-1 is about 6 times faster for PI attached to the mesophenyl than for PI attached to the P-phenyl, the opposite is observed for charge separation from S-2. Subsequent charge recombination is 2.6-2.8 times faster for PI attached to the meso-phenyl relative to that of the beta-phenyl. Comparisons of rates between MTHF and toluene show that the ordering of rates is the same for both solvents, although the rate ratios are larger in MTHF than in toluene.