Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid

被引:14
|
作者
Xia, Debin [1 ,2 ]
Keerthi, Ashok [2 ,3 ]
An, Cunbin [2 ]
Baumgarten, Martin [2 ]
机构
[1] Harbin Inst Technol, MIIT Key Lab Crit Mat Technol New Energy Convers, Sch Chem & Chem Engn, Harbin 150001, Peoples R China
[2] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany
[3] Univ Manchester, Sch Phys & Astron, Condensed Matter Phys Grp, Manchester M13 9PL, Lancs, England
来源
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 01期
关键词
FIELD-EFFECT TRANSISTORS; GROUND-STATE; HIGH-PERFORMANCE; HYDROCARBONS; OLIGOTHIOPHENES; SEMICONDUCTOR; DIRADICALS; MOLECULES; RADICALS; DESIGN;
D O I
10.1039/c6qo00543h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A fused heteroacene derivative, bis(dicyanomethylene)-end-capped-dithieno[2,3-d;2',3'-d]benzo[2,1-b;3,4-b']-dithiophene (4CN-DTmBDT) was synthesized. Its open-shell biradical character in the ground state is studied by a combination of electron paramagnetic resonance (EPR) and nuclear magnetic resonance (NMR). Structural assignment was verified with single crystal X-ray diffraction analysis. A highly stable biradicaloid with a low energy gap and low LUMO level is achieved.
引用
收藏
页码:18 / 21
页数:4
相关论文
共 50 条
  • [41] SYNTHESIS OF PYRIDO[3,4-B]-AND AZEPINO[3,4-B]PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES FROM 2-(1-PYRAZOLYL)PURINE
    GLUSHKOV, RG
    ZASOSOVA, IM
    OVCHAROVA, IM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1977, (10): : 1398 - 1403
  • [42] Electrosynthesis and characterization of a novel electrochromic copolymer of N-methylpyrrole with cyclopenta[2,1-b:3,4-b′]dithiophene
    Fu, Yunzhi
    Cheng, Xinfeng
    Zhao, Jinsheng
    Kong, Tianyu
    Cui, Chuansheng
    Zhang, Xianxi
    POLYMER JOURNAL, 2012, 44 (10) : 1048 - 1055
  • [43] Highly efficient and facile alkylation of 4H-cyclopenta-[2,1-b:3,4-b′]dithiophene in water
    Iyer, Parameswar Krishnan (pki@iitg.ernet.in), 1600, Royal Society of Chemistry (40):
  • [44] CRYSTAL STRUCTURE OF 4H-CYCLOPENTA[2,1-B - 3,4-B']DITHIOPHENE AT 160 DEGREES C
    KOSTER, PB
    VANBOLHU.F
    VISSER, GJ
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1970, B 26 (DEC15): : 1932 - &
  • [45] Highly efficient and facile alkylation of 4H-cyclopenta-[2,1-b:3,4-b′] dithiophene in water
    Raju, Telugu Bhim
    Gopikrishna, Peddaboodi
    Iyer, Parameswar Krishnan
    RSC ADVANCES, 2014, 4 (71): : 37738 - 37745
  • [46] Alternating Copolymers Incorporating Cyclopenta[2,1-b:3,4-b′]dithiophene Unit and Organic Dyes for Photovoltaic Applications
    Cheng, Yen-Ju
    Hung, Lung-Chang
    Cao, Fong-Yi
    Kao, Wei-Shun
    Chang, Chih-Yu
    Hsu, Chain-Shu
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (08) : 1791 - 1801
  • [47] Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dthiophenes with NBS-a route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones
    Marin, Lidia
    Van Mierloo, Sarah
    Zhang, Yuexing
    Robeyns, Koen
    Champagne, Benoit
    Adriaensens, Peter
    Lutsen, Laurence
    Vanderzande, Dirk
    Maes, Wouter
    TETRAHEDRON, 2013, 69 (10) : 2260 - 2267
  • [48] Electrosynthesis and characterization of a novel electrochromic copolymer of N-methylpyrrole with cyclopenta[2,1-b:3,4-b′]dithiophene
    Yunzhi Fu
    Xinfeng Cheng
    Jinsheng Zhao
    Tianyu Kong
    Chuansheng Cui
    Xianxi Zhang
    Polymer Journal, 2012, 44 : 1048 - 1055
  • [49] Electrochemical Synthesis and Characterization of a Novel Electrochromic Copolymer of 4H-cyclopenta[2,1-b:3,4-b′]Dithiophene with Pyrene
    Yang, Wei
    Zhao, Jinsheng
    Kong, Ying
    Kong, Tianyu
    Cui, Chuansheng
    INTERNATIONAL JOURNAL OF ELECTROCHEMICAL SCIENCE, 2012, 7 (04): : 2764 - 2780
  • [50] The Efficient Synthesis of Dithieno[3,4-b:3′,4′-d]thiophene
    Xu, Li
    Wang, Zhen
    Xu, Kun
    Shi, Jianwu
    Wang, Hua
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (06) : 474 - 477