N,N-bis(1-ethylpropyl)-2,5,8,11-tetraphenyl perylenediimide | 1192464-27-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: N,N-bis(1-ethylpropyl)-2,5,8,11-tetraphenyl perylenediimide
• 英文别名: N,N'-bis(1-ethylpropyl)-2,5,8,11-tetraphenylperylene-3,4:9,10-tetracarboxylic acid bisimide；7,18-Di(pentan-3-yl)-10,15,21,25-tetraphenyl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• CAS: 1192464-27-9
• 化学式: C₅₈H₄₆N₂O₄
• 分子量: 835.014
• InChiKey: HRYDLOAMLKFZOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  64
• 可旋转键数：
  10
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5,5-二甲基-2-苯基-1,3,2-二氧硼杂 、 2,9-二(3-戊烷基)异喹啉并[4',5',6':6,5,10]蒽并[2,1,9-def]异喹啉-1,3,8,10(2H,9H)-四酮 在 RuH₂(CO)(PPh₃)₃ 作用下， 以 均三甲苯 为溶剂， 反应 40.0h， 以59%的产率得到N,N-bis(1-ethylpropyl)-2,5,8,11-tetraphenyl perylenediimide
  参考文献：
  名称：

  在无重原子的im二酰亚胺中进入三重态

  摘要：

  per二酰亚胺（PDI）的先前研究主要利用最低的单重态激发态S 1。在PDI中三重激发态（T 1）的产生对于从光动力疗法到光伏技术的应用非常重要。但是，这仍然是一项艰巨的任务。本文中，我们开发了一种无重原子的策略，通过在缺电子的per二酰亚胺（PDI）核的头部位置引入供电子性芳基（Ar）来促进T 1 ←S 1系统间交叉（ISC）。我们发现，ISC的效率通过增加苯基取代的芳基的供电子能力从8％提高到54％，然后提高到86％（p-PDI）转化为甲氧基苯基（MeO-PDI），然后转化为甲硫基二甲苯（MeS-PDI）。通过提高分子内电荷转移（ICT）相互作用从p -PDI到的MeO-PDI，再到MES-PDI，经由能量转移反应的单线态氧产生在T 1 PDI的至3 ö 2与最高产量证明高达80％。这些结果为开发用于光电子应用的新型三重态PDI和相关的二甲苯二酰亚胺提供了指南。

  DOI：

  10.1002/chem.201600300

文献信息

• Synthesis of Arylated Perylene Bisimides through C−H Bond Cleavage under Ruthenium Catalysis
  作者：Satomi Nakazono、Shanmugam Easwaramoorthi、Dongho Kim、Hiroshi Shinokubo、Atsuhiro Osuka

  DOI：10.1021/ol902271b

  日期：2009.12.3

  Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The electronic nature of the introduced aryl substituents has a significant impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive

  在钌催化剂的存在下，用各种芳基硼酸酯处理per双酰亚胺（PBI），可以在2,5,8,11-位上以良好的产率和良好的区域选择性提供四芳基化的PBI。引入的芳基取代基的电子性质对其光学和电子性质具有重大影响。该方案已应用于水溶性发射性PBI衍生物的合成。
• Photoinduced Electron Transfer in 2,5,8,11-Tetrakis-Donor-Substituted Perylene-3,4:9,10-bis(dicarboximides)
  作者：Leah E. Shoer、Samuel W. Eaton、Eric A. Margulies、Michael R. Wasielewski

  DOI：10.1021/jp511624s

  日期：2015.6.18

  A series of electron donor-acceptor compounds based on substitution of perylene-3,4:9,10,bis(dicarboximide) (PDI) with four electron donors at the 2,5,8,11-positions were synthesized and characterized using femtosecond transient absorption spectroscopy. The distance between the PDI and the N,N-dimethylaniline or phenothiazine donors was varied using one or two phenyl groups. Photoexcitation of PDI results in rapid charge separation followed by charge recombination with time constants ranging from tens of picoseconds to nanoseconds. The electron transfer time constants are compared with those of the corresponding molecules in which the donor is attached to the PDI through its imide nitrogen atom. The electron transfer reactions through the 2,5,8,11-positions of PDI are generally much faster than those through the imide nitrogen positions, in concert with stronger donor electronic coupling to the PDI acceptor core and in contrast to substituents at the imide positions through which the HOMO and LUMO nodal planes pass.