N,N'-bis(1-ethylpropyl)-2,5,8,11-tetrakis(p-methylphenyl)perylenediimide | 1192464-35-9

• 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-tetrakis(p-methylphenyl)perylenediimide
• 英文别名: mp-PDI；N,N'-bis(1-ethylpropyl)-2,5,8,11-tetrakis(p-methylphenyl)perylene-3,4:9,10-tetracarboxylic acid bisimide；10,15,21,25-Tetrakis(4-methylphenyl)-7,18-di(pentan-3-yl)-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；10,15,21,25-tetrakis(4-methylphenyl)-7,18-di(pentan-3-yl)-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: 1192464-35-9
• 化学式: C₆₂H₅₄N₂O₄
• 分子量: 891.122
• InChiKey: DHKQMLTXBNYFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.4
• 重原子数：
  68
• 可旋转键数：
  10
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  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 、 4-甲基苯硼酸新戊基二醇酯 在 RuH₂(CO)(PPh₃)₃ 作用下， 以 频哪酮 、 均三甲苯 为溶剂， 反应 35.0h， 以69%的产率得到N,N'-bis(1-ethylpropyl)-2,5,8,11-tetrakis(p-methylphenyl)perylenediimide
  参考文献：
  名称：

  钌催化下的CH键裂解合成丙烯酸化的Per双酰亚胺

  摘要：

  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。

  DOI：

  10.1021/ol902271b

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。
• Self-Assembled Microdisk Lasers of Perylenediimides
  作者：Zhenyi Yu、Yishi Wu、Qing Liao、Haihua Zhang、Shuming Bai、Hui Li、Zhenzhen Xu、Chunlin Sun、Xuedong Wang、Jiannian Yao、Hongbing Fu

  DOI：10.1021/jacs.5b10353

  日期：2015.12.9

  Organic solid-state lasers (OSSLs) have been a topic of intensive investigations. Perylenediimide (PDI) derivatives are widely used in organic thin-film transistors and solar cells. However, OSSLs based on neat PDIs have not been achieved yet, owing to the formation of H-aggregates and excimer trap-states. Here, we demonstrated the first PDI-based OSSL from whispering-gallery mode (WGM) hexagonal microdisk (hMD) microcavity of N,N'-bis(1-ethylpropyl)-2,5,8,11-tetrakis(p-methyl-phenyl)-perylenediimide (mp-PDI) self-assembled from solution. Single-crystal data reveal that mp-PDI molecules stack into a loosely packed twisted brickstone arrangement, resulting in J-type aggregates that exhibit a solid-state photoluminescence (PL) efficiency phi > 15%. Moreover, we found that exciton-vibration coupling in J-aggregates leads to an exceptional ultrafast radiative decay, which reduces the exciton diffusion length, in turn, suppresses bimolecular exciton annihilation (bmEA) process. These spectral features, plus the optical feedback provided by WGM-hMD microcavity, enable the observation of multimode lasing as evidenced by nonlinear output, spectral narrowing, and temporal coherence of laser emission. With consideration of high carrier-mobility associated with PDIs, hMDs of mp-PDI are attractive candidates on the way to achieve electrically driven OSSL.