Novel synthesis of 5-methyl-5,10-dihydroindolo-[3,2-b]indoles by Pd-catalyzed C-C and two-fold C-N coupling reactions

被引:34
作者
Tran Quang Hung [1 ]
Hancker, Soeren [1 ]
Villinger, Alexander [1 ]
Lochbrunner, Stefan [2 ]
Tuan Thanh Dang [1 ]
Friedrich, Aleksej [2 ]
Breitsprecher, Wolfgang [2 ]
Langer, Peter [1 ,3 ]
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Univ Rostock, Inst Phys, D-18051 Rostock, Germany
[3] Univ Rostock eV LIKAT, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
FIELD-EFFECT TRANSISTORS; ORGANIC SEMICONDUCTORS; FLUORESCENCE; DERIVATIVES; INDOLE; HETEROACENES; HETEROCYCLES; PERFORMANCE; CORE;
D O I
10.1039/c4ob01723d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 5,10-dihydroindolo[3,2-b]indoles was successfully prepared by an efficient two-step strategy based on site-selective Pd-catalyzed cross-coupling reaction with N-methyl-2,3-dibromoindole and subsequent cyclization by two-fold Pd-catalyzed C-N coupling with amines. The products show a strong fluorescence.
引用
收藏
页码:583 / 591
页数:9
相关论文
共 34 条
  • [1] Functionalized acenes and heteroacenes for organic electronics
    Anthony, John E.
    [J]. CHEMICAL REVIEWS, 2006, 106 (12) : 5028 - 5048
  • [2] Asiri AM, 2012, B KOREAN CHEM SOC, V33, P1900
  • [3] Bach T, 1999, EUR J ORG CHEM, V1999, P2045
  • [4] Synthesis and properties of B,N-bridged p-terphenyls
    Chen, Dong-Mei
    Qin, Qian
    Sun, Zuo-Bang
    Peng, Qian
    Zhao, Cui-Hua
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (07) : 782 - 784
  • [5] Azadibenzophospholes: Functional Building Blocks with Pronounced Electron-Acceptor Character
    Durben, Stefan
    Baumgartner, Thomas
    [J]. INORGANIC CHEMISTRY, 2011, 50 (14) : 6823 - 6836
  • [6] Quasi-Molecular Fluorescence from Graphene Oxide
    Galande, Charudatta
    Mohite, Aditya D.
    Naumov, Anton V.
    Gao, Wei
    Ci, Lijie
    Ajayan, Anakha
    Gao, Hui
    Srivastava, Anchal
    Weisman, R. Bruce
    Ajayan, Pulickel M.
    [J]. SCIENTIFIC REPORTS, 2011, 1
  • [7] Hole mobility in organic single crystals measured by a "flip-crystal" field-effect technique
    Goldmann, C
    Haas, S
    Krellner, C
    Pernstich, KP
    Gundlach, DJ
    Batlogg, B
    [J]. JOURNAL OF APPLIED PHYSICS, 2004, 96 (04) : 2080 - 2086
  • [8] GRINYOV AN, 1982, KHIM GETEROTSIKL+, P199
  • [9] GRINYOV AN, 1982, KHIM GETEROTSIKL+, P201
  • [10] Heller G., 1917, BERICHTE DTSCH CHEM, V50, P1202