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
  • [31] Use of sodium salt of cyclic β-formylester for synthesis of dihydro-2H-furo[2,3-d]pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines
    Patil, Shivaraj P.
    Toche, Raghunath B.
    MONATSHEFTE FUR CHEMIE, 2011, 142 (11): : 1193 - 1201
  • [32] Use of sodium salt of cyclic β-formylester for synthesis of dihydro-2H-furo[2,3-d]pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines
    Shivaraj P. Patil
    Raghunath B. Toche
    Monatshefte für Chemie - Chemical Monthly, 2011, 142 : 1193 - 1201
  • [33] The Use of Cyclopenta[2,1-b;3,4-b′]dithiophene Analogues for the Development of Low-Bandgap Materials
    Willot, Pieter
    De Cremer, Lieven
    Koeckelberghs, Guy
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2012, 213 (12) : 1216 - 1224
  • [34] X-Shaped donor molecules based on benzo[2,1-b:3,4-b′]dithiophene as organic solar cell materials with PDIs as acceptors
    Bibi, Shamsa
    Li, Ping
    Zhang, Jingping
    JOURNAL OF MATERIALS CHEMISTRY A, 2013, 1 (44) : 13828 - 13841
  • [35] Dithieno[2,3-d;2′,3′-d′]benzo[1,2-b;4,5-b′]-dithiophene based organic sensitizers for dye-sensitized solar cells
    Guo, Xin
    Tsao, Hoi Nok
    Gao, Peng
    Xia, Debin
    An, Cunbin
    Nazeeruddin, Mohammad Khaja
    Baumgarten, Martin
    Graetzel, Michael
    Muellen, Klaus
    RSC ADVANCES, 2014, 4 (96): : 54130 - 54133
  • [36] THE CHEMISTRY OF NOVEL C-2 DIAZABIARYL LIGANDS - CYCLOOCTA[2,1-B/3,4-B']DIPYRIDINE, CYCLOOCTA[2,1-B/3,4-B']DIQUINOLINE AND THEIR RELATED-COMPOUNDS
    WANG, XC
    WONG, HNC
    TETRAHEDRON, 1995, 51 (25) : 6941 - 6960
  • [37] Synthesis and characterization of a series of low-bandgap copolymers based on cyclopenta[2,1-b:3,4-b′]dithiophene and thienopyrroledione for photovoltaic applications
    Hong, Young-Rae
    Ng, Joo Yee
    Wong, Hoi Ka
    Moh, Lionel C. H.
    Yip, Yong Jie
    Chen, Zhi-Kuan
    Norsten, Tyler B.
    SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2012, 102 : 58 - 65
  • [38] Microribbon Field-Effect Transistors Based on Dithieno[2,3-d;2,3′-d]benzo[1,2-b;4,5-b′]dithiophene Processed by Solvent Vapor Diffusion
    Wang, Suhao
    Gao, Peng
    Liebewirth, Ingo
    Kirchhoff, Katrin
    Pang, Shuping
    Feng, Xinliang
    Pisula, Wojciech
    Muellen, Klaus
    CHEMISTRY OF MATERIALS, 2011, 23 (22) : 4960 - 4964
  • [39] Dithieno[2,3-d:2',3'-d']benzo[1,2-b:4,5-b']dithiophene (DTBDAT)-based copolymers for high-performance organic solar cells
    Lee, Ye Seul
    Song, Seyeong
    Yoon, Yung Jin
    Lee, Yun-Ji
    Kwon, Soon-Ki
    Kim, Jin Young
    Kim, Yun-Hi
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2016, 54 (19) : 3182 - 3192
  • [40] A novel polymer donor based on dithieno[2,3-d:2′,3′-d′′]benzo[1,2-b:4,5-b′]dithiophene for highly efficient polymer solar cells
    Huang, Jiaming
    Peng, Ruixiang
    Xie, Lingchao
    Song, Wei
    Hong, Ling
    Chen, Sanhui
    Wei, Qiang
    Ge, Ziyi
    JOURNAL OF MATERIALS CHEMISTRY A, 2019, 7 (06) : 2646 - 2652