1-nitroperylene bisimide | 1257079-45-0

• 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: 1-nitroperylene bisimide
• 英文别名: N,N-dicyclohexyl-(1-nitro)perylene-3,4,9,10-tetracarboxylic acid bisimide；7,18-Dicyclohexyl-11-nitro-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: 1257079-45-0
• 化学式: C₃₆H₂₉N₃O₆
• 分子量: 599.643
• InChiKey: NKWIINSHUYJVRD-UHFFFAOYSA-N

物化性质

• 密度：
  1.520±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  45
• 可旋转键数：
  2
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-nitroperylene bisimide 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 氯仿 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Facile synthesis and replacement reactions of mono-substituted perylene bisimide dyes

  摘要：

  Mono-substituted perylene bisimides were synthesized in high yields under mild condition. The starting material was mono-nitrified perylene bisimides instead of usual perylene bisimides halogenated at different levels. Besides phenols and amine, the nucleophilic reagents included alcohol and thiol. The substitution of nitro group was easier and more effective than the substitution of halogen atoms. But the substitution reaction of pyrrolidine afforded mono-and 1,6-disubstituted perylene bisimides owing to the high activity of nitrified perylene bisimides and pyrrolidine. Several replacement reactions between phenols and alcohol based on phenol mono-substituted perylene bisimide were also found. The replacement reactions between phenols was fast and in high yield. The absorption of the mono-substituted perylene bisimides were tunable in the whole visible region. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.05.009
• 作为产物：
  描述：

  2,9-二(环己基)-蒽并[2,1,9-def:6,5,10-D'e'f']二异喹啉-1,3,8,10-四酮 在 ammonium cerium (IV) nitrate 、 硝酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到1-nitroperylene bisimide
  参考文献：
  名称：

  通过与苝二亚胺聚集体结合，增强可见光驱动的染料降解和光催化 H2 在 MoS2 上的析出

  摘要：

  利用高效廉价的催化剂去除废水中的有机污染物和光催化析氢最近引起了极大的关注。在此，MoS 2纳米花（MoS 2 NFs）和1-苯酚-苝二酰亚胺微带（PPDI MBs）分别通过水热和溶剂交换工艺制备。通过水热法将它们紧密混合以获得新型有机-无机 MoS 2 /PPDI p-n 异质结光催化剂（MoS 2 /PPDI HSs）。值得注意的是，优化后的 MoS 2/PPDI HS 催化剂对甲基橙 (MO)、亚甲蓝 (MB) 和铬黑 T (EBT) 表现出高效的光催化活性。同时，新复合材料表现出更好的析氢反应活性。光催化活性的显着增强是由于形成了 Z 型 p-n 异质结和大的比表面积，可以有效地分离和转移界面电荷。自由基清除技术证实超氧自由基阴离子 (˙O 2 − ) 和空穴 (h +) 在光催化过程中发挥了重要作用。该研究表明，这种新型复合材料由于合成工艺简单廉价、原料成本低和方法环保，在解决环境和能源问题方面具有广泛的应用前景。

  DOI：

  10.1039/d1nj01999f

文献信息

• Synthesis and properties of bay unilaterally extended and mono-substituted perylene diimides
  作者：Fengxia Zhang、Xianqiang Huang、Xiaofeng Wei、Huixue Ren、Tianyi Jiang、Xuemei Li、Junsen Wu、Yongshan Ma

  DOI：10.1177/1747519819886502

  日期：2020.1

  sulfoxide-containing perylene diimide, 1-propyl sulfoxide-N,N′-dicyclohexylperylene-3,4,9,10-tetracarboxylic diimide (3), are reported. The photophysical, electrochemical, aggregation, and thermal properties of these compounds are investigated by ultraviolet visible absorption, fluorescence, cyclic voltammetric, X-ray diffraction, and thermogravimetric analysis techniques. The geometries of the compounds

  两种硫修饰的苝二酰亚胺、五元 S-杂环环化苝二酰亚胺 (1) 和 1-丙硫醇-N,N'-二环己基苝-3,4,9,10-四羧酸二酰亚胺 (2) 的合成，以及报道了一种新型的含亚砜的苝二酰亚胺，1-丙基亚砜-N,N'-二环己基苝-3,4,9,10-四羧酸二酰亚胺 (3)。通过紫外可见吸收、荧光、循环伏安法、X 射线衍射和热重分析技术研究了这些化合物的光物理、电化学、聚集和热性质。使用密度泛函理论在 6-31G* 理论水平上优化了化合物的几何形状，并且它们的潜力与分子轨道相关。
• Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides
  作者：Kew-Yu Chen、Tzu-Chien Fang、Ming-Jen Chang

  DOI：10.1016/j.dyepig.2011.06.023

  日期：2012.1

  1-Aminoperylene bisimides (1a–1c) were synthesized under mild condition in high yields, and were characterized by FT-IR, 1H NMR, UV–Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetric analyses. These compounds are stable up to 310 °C according to thermogravimetric analyses. They undergo two quasi-reversible one-electron oxidations and two quasi-reversible

  1-氨基oper亚双酰亚胺（1a – 1c）在温和的条件下以高收率合成，并通过FT-IR，1 H NMR，UV-Vis，HRMS光谱，循环伏安法，差示扫描量热法和热重分析进行了表征。根据热重分析，这些化合物可在高达310°C的温度下保持稳定。它们在中等电位下在二氯甲烷中经历两次准可逆的单电子氧化和两次准可逆的单电子还原。报告了它们在各种条件下的光谱性质和互补密度泛函理论（DFT）计算。
• 1,6-Dinitroperylene Bisimide Dyes: Synthesis, Characterization and Photophysical Properties
  作者：Che-Wei Chang、Hsing-Yang Tsai、Kew-Yu Chen

  DOI：10.1002/jccs.201300517

  日期：2014.4

  7‐regioisomers of dinitro‐substituted perylene bisimides (1a—1b and 2a—2b) were synthesized under mild condition in high yields. The 1,6‐ and 1,7‐regioisomers were successfully isolated from the regioisomeric mixture using conventional methods of separation and subsequently characterized by 500 MHz 1H NMR spectroscopy. This is the first time when 1,6‐dinitroperylene bisimides (1a—1b) are obtained in pure form.

  在温和的条件下以高收率合成了二硝基取代的bi双酰亚胺（1a - 1b和2a - 2b）的1,6-和1,7-区域异构体。使用常规分离方法成功地从区域异构体混合物中分离出1,6和1,7-区域异构体，然后通过500 MHz 1 H NMR光谱进行了表征。这是首次获得纯净的1,6-二硝基nitro双酰亚胺（1a - 1b）。此外，发现1和2的光物理和电化学性质几乎相同。硝基官能团提供n的稳定性通过降低LUMO来抵抗环境氧化，从而可以在空气稳定的n型有机半导体中提供潜在的应用。
• Efficient energy-level modification of novel pyran-annulated perylene diimides for photocatalytic water splitting
  作者：Ran Wang、Gang Li、Andong Zhang、Wen Wang、Guanwei Cui、Jianfeng Zhao、Zhiqiang Shi、Bo Tang

  DOI：10.1039/c7cc03682e

  日期：——

  This work reports a facile method to prepare pyran-annulated perylene diimides, which are used as photocatalysts in photocatalytic water splitting.

  这项工作报告了一种简便的方法，用于制备吡喃-环戊二酰亚胺衍生的苝，这些苝被用作光催化剂进行光催化水分解。
• Self-assembled nanorods of bay functionalized perylenediimide: Cu²⁺ based ‘turn-on’ response for INH, complementary NOR/OR and TRANSFER logic functions and fluorosolvatochromism
  作者：Prabhpreet Singh、Kapil Kumar、Gaurav Bhargava、Subodh Kumar

  DOI：10.1039/c6tc00422a

  日期：——

  Self-assembled nanorods shows disassembly and inhibition of the ICT/PET process with Cu²⁺ for developing INH, complimentary NOR/OR and TRANSFER logic functions and fluorosolvatochromism

  自组装纳米棒显示与Cu²⁺的ICT/PET过程的解离和抑制，用于开发INH、互补NOR/OR和TRANSFER逻辑功能以及荧光溶剂化色谱。