Facile Synthesis of Nitrogen-containing Polycyclic Aromatic Hydrocarbons from Perylene Bisimides

被引：6
|
作者：
Ito, Satoru [1 ]
Hiroto, Satoru [1 ]
Shinokubo, Hiroshi [1 ]
机构：
[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4648603, Japan
来源：
CHEMISTRY LETTERS | 2014年 / 43卷 / 08期
关键词：
ELECTRONIC-PROPERTIES; ORGANIC ELECTRONICS; FAMILY; IMIDES; AZINE;
D O I：
10.1246/cl.140330
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have developed a facile procedure for the synthesis of pi-extended fluorubins from perylene bisimides. Iridium-catalyzed direct borylation, the Suzuki-Miyaura cross-coupling, and an acid-condensation sequence afforded pi-extended fluorubins 1 in moderate yields. X-ray diffraction analysis revealed a planar structure of 1. In addition, optical analysis and DFT calculations indicated the presence of intramolecular charge-transfer interactions in 1c.
引用
收藏
页码：1309 / 1311
页数：3
相关论文
共 50 条
  • [21] The Synthesis of Aromatic Hydrazones as Nitrogen-Containing Prostaglandin Congeners
    Guo Hao XIE
    Yan Mei HE
    Yuan Liu WU(Institute of Materia Medica
    Chinese Chemical Letters, 1998, (06) : 529 - 531
  • [22] IDENTIFICATION OF PARTIALLY HYDROGENATED NITROGEN-CONTAINING POLYCYCLIC AROMATIC-HYDROCARBONS IN COAL LIQUIDS BY TANDEM MASS-SPECTROMETRY
    WOOD, KV
    SCHMIDT, CE
    COOKS, RG
    BATTS, BD
    ANALYTICAL CHEMISTRY, 1984, 56 (08) : 1335 - 1338
  • [23] One-Pot Facile Synthesis of Pyridyl Annelated Perylene Bisimides
    Jiang, Wei
    Li, Yan
    Yue, Wan
    Zhen, Yonggang
    Qu, Jianqiang
    Wang, Zhaohui
    ORGANIC LETTERS, 2010, 12 (02) : 228 - 231
  • [24] A Luminescent Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity
    Gu, Xinggui
    Wang, Hong
    Roose, Jesse
    He, Zikai
    Zhou, Yue
    Yan, Yongli
    Cai, Yuanjing
    Shi, Heping
    Zhang, Yilin
    Sung, Herman H. Y.
    Lam, Jacky W. Y.
    Miao, Qian
    Zhao, Yongsheng
    Wong, Kam Sing
    Williams, Ian D.
    Tang, Ben Zhong
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (49) : 17973 - 17980
  • [25] STUDY OF THERMAL-STABILITY IN SERIES OF AROMATIC AND NITROGEN-CONTAINING POLYCYCLIC COMPOUNDS
    KORSHAK, VV
    KHOMUTOV, VA
    DOROSHENKO, YE
    VYSOKOMOLEKULYARNYE SOEDINENIYA SERIYA A, 1976, 18 (03): : 523 - 527
  • [26] Does glucose enhance the formation of nitrogen containing polycyclic aromatic compounds and polycyclic aromatic hydrocarbons in the pyrolysis of proline?
    Britt, PF
    Buchanan, AC
    Owens, CV
    Skeen, JT
    FUEL, 2004, 83 (11-12) : 1417 - 1432
  • [27] A simple protocol for the synthesis of perylene bisimides from perylene tetracarboxylic dianhydride
    Marinho, Elina
    Figueiredo, Pedro R.
    Araujo, Rui
    Proenca, M. Fernanda
    RSC ADVANCES, 2024, 14 (16) : 11141 - 11150
  • [28] EFFECT OF PYROLYSIS CONDITIONS ON THE COMPOSITION OF NITROGEN-CONTAINING POLYCYCLIC AROMATIC-COMPOUNDS FROM A BITUMINOUS COAL
    WORNAT, MJ
    SAROFIM, AF
    LONGWELL, JP
    LAFLEUR, AL
    ENERGY & FUELS, 1988, 2 (06) : 775 - 782
  • [29] Annulative π-extension of indoles and pyrroles with diiodobiaryls by Pd catalysis: rapid synthesis of nitrogen-containing polycyclic aromatic compounds
    Kitano, Hiroyuki
    Matsuoka, Wataru
    Ito, Hideto
    Itami, Kenichiro
    CHEMICAL SCIENCE, 2018, 9 (38) : 7556 - 7561
  • [30] Synthesis of nitrogen-containing heterocyclic compounds by photooxidation of aromatic azides
    Chainikova, Ekaterina
    Safiullin, Rustam
    Spirikhin, Leonid
    Erastov, Alexey
    TETRAHEDRON LETTERS, 2013, 54 (17) : 2140 - 2142
12345