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 30 条
  • [1] ANOMALOUS PARAMAGNETISM OF COPPER ACETATE
    BLEANEY, B
    BOWERS, KD
    [J]. PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES A-MATHEMATICAL AND PHYSICAL SCIENCES, 1952, 214 (1119): : 451 - 465
  • [2] 6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics, and Ambipolar OFETs
    Chase, Daniel T.
    Fix, Aaron G.
    Kang, Seok Ju
    Rose, Bradley D.
    Weber, Christopher D.
    Zhong, Yu
    Zakharov, Lev N.
    Lonergan, Mark C.
    Nuckolls, Colin
    Haley, Michael M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10349 - 10352
  • [3] Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes
    Chase, Daniel T.
    Rose, Bradley D.
    McClintock, Sean P.
    Zakharov, Lev N.
    Haley, Michael M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1127 - 1130
  • [4] Organic Radicals As Spin Filters
    Herrmann, Carmen
    Solomon, Gemma C.
    Ratner, Mark A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) : 3682 - +
  • [5] A Stable π-Conjugated Singlet Biradical
    Hinkel, Felix
    Freudenberg, Jan
    Bunz, Uwe H. F.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (34) : 9830 - 9832
  • [6] Dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]dithiophene: a novel building-block for a planar copolymer
    Keerthi, Ashok
    An, Cunbin
    Li, Mengmeng
    Marszalek, Tomasz
    Ricciardulli, Antonio Gaetano
    Radha, Boya
    Alsewailem, Fares D.
    Muellen, Klaus
    Baumgarten, Martin
    [J]. POLYMER CHEMISTRY, 2016, 7 (08) : 1545 - 1548
  • [7] N-Substituted Dicyanomethylphenyl Radicals: Dynamic Covalent Properties and Formation of Stimuli-Responsive Cyclophanes by Self-Assembly
    Kobashi, Toshiyuki
    Sakamaki, Daisuke
    Seki, Shu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) : 8634 - 8638
  • [8] Five-Ring Fused Tetracyanothienoquinoids as High-Performance and Solution-Processable n-Channel Organic Semiconductors: Effect of the Branching Position of Alkyl Chains
    Li, Jie
    Qiao, Xiaolan
    Xiong, Yu
    Li, Hongxiang
    Zhu, Daoben
    [J]. CHEMISTRY OF MATERIALS, 2014, 26 (19) : 5782 - 5788
  • [9] Tetrabenzo[a,f,j,o]perylene: A Polycyclic Aromatic Hydrocarbon With An Open-Shell Singlet Biradical Ground State
    Liu, Junzhi
    Ravat, Prince
    Wagner, Manfred
    Baumgarten, Martin
    Feng, Xinliang
    Mueller, Klaus
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) : 12442 - 12446
  • [10] Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications
    Mishra, Amaresh
    Ma, Chang-Qi
    Baeuerle, Peter
    [J]. CHEMICAL REVIEWS, 2009, 109 (03) : 1141 - 1276