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
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
  • [1] Fate and behaviour of nitrogen-containing polycyclic aromatic hydrocarbons in soil
    Anyanwu, Ihuoma N.
    Semple, Kirk T.
    ENVIRONMENTAL TECHNOLOGY & INNOVATION, 2015, 3 : 108 - 120
  • [2] Occurrence and Distribution of Polycyclic Aromatic Hydrocarbons and Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Analogues in Soils from the Niger Delta, Nigeria
    Anyanwu, Ihuoma N.
    Semple, Kirk T.
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (09) : 6290 - 6302
  • [3] Selective fluorescence quenching of nitrogen-containing polycyclic aromatic hydrocarbons by aliphatic amines
    Li, XP
    McGuffin, VL
    ANALYTICA CHIMICA ACTA, 2004, 526 (02) : 155 - 162
  • [4] The Topogical Model of the Chromatographic Retention Index of Nitrogen-Containing Polycyclic Aromatic Hydrocarbons
    Chen, Yan
    Feng, Changjun
    Ding, Xiaotao
    PROCEEDINGS OF THE INTERNATIONAL CONFERENCE ON ADVANCES IN ENERGY, ENVIRONMENT AND CHEMICAL ENGINEERING, 2015, 23 : 784 - 788
  • [5] Synthesis of functionalized nitrogen-containing polycyclic aromatic hydrocarbons and other prebiotic compounds in impacting glycine solutions
    Kroonblawd, Matthew P.
    Lindsey, Rebecca K.
    Goldman, Nir
    CHEMICAL SCIENCE, 2019, 10 (24) : 6091 - 6098
  • [6] Nitrogen-containing polycyclic aromatic hydrocarbons (PAHs) with bowl-shaped structures: synthesis, architecture, and applications
    Chen, Xu-Lang
    Yu, Si-Qian
    Liang, Jia-Qi
    Huang, Xiaohuan
    Gong, Han-Yuan
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (04): : 1340 - 1354
  • [7] IDENTIFICATION AND QUANTITATIVE-ANALYSIS OF NITROGEN-CONTAINING POLYCYCLIC AROMATIC-HYDROCARBONS IN SEDIMENTS
    ONUSKA, FI
    TERRY, KA
    HRC-JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY, 1989, 12 (06): : 362 - 367
  • [8] Toxicity of nitrogen-containing polycyclic aromatic hydrocarbons (NPAH) to the midge Chironomus riparius (Diptera)
    Bleeker, EAJ
    BuckertdeJong, MC
    vanderGeest, HG
    Kraak, MHS
    PROCEEDINGS OF THE SECTION EXPERIMENTAL AND APPLIED ENTOMOLOGY OF THE NETHERLANDS ENTOMOLOGICAL SOCIETY (N.E.V.), VOL 7, 1996, 1996, : 197 - 202
  • [9] Synthesis of aromatic hydrocarbons containing a perylene core
    Marquez, Gerardo B.
    Clevenger, Robert
    Silva, Linda C.
    Kilway, Kathleen V.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [10] Titanocene-Mediated Dinitrile Coupling: A Divergent Route to Nitrogen-Containing Polycyclic Aromatic Hydrocarbons
    Kiel, Gavin R.
    Samkian, Adrian E.
    Nicolay, Amelie
    Witzke, Ryan J.
    Tilley, T. Don
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (07) : 2450 - 2454