Facile synthesis and properties of dithieno[3,2-b:2′,3′-d]arsoles

被引:52
作者
Kato, Takuji [1 ]
Imoto, Hiroaki [1 ]
Tanaka, Susumu [1 ]
Ishidoshiro, Makoto [1 ]
Naka, Kensuke [1 ]
机构
[1] Kyoto Inst Technol, Grad Sch Sci & Technol, Fac Mol Chem & Engn, Sakyo Ku, Goshokaido Cho, Kyoto 6068585, Japan
关键词
FIELD-EFFECT TRANSISTORS; PI-CONJUGATED POLYMERS; MOLECULAR-STRUCTURE; CHARGE-TRANSPORT; BUILDING-BLOCK; HOST MATERIALS; SOLAR-CELLS; PERFORMANCE; EMISSION; EFFICIENCY;
D O I
10.1039/c6dt02034h
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Dithieno[3,2-b: 2', 3'-d]arsoles have been synthesized via a safe and easy synthetic procedure, in which volatile arsenic intermediates are excluded. The obtained dithienoarsole derivatives were stable in the ambient atmosphere, unlike their phosphorus analogues, dithienophospholes. The Suzuki-Miyaura coupling reaction is applicable for structural modification and expansion of the pi-conjugated system, and carried out the polymerization of the compounds. Dithienoarsoles showed an intense emission not only in solution but also in the solid state, and their molecular packing was analyzed by X-ray crystallography. The main-chain type dithienoarsole polymer formed a luminescent film. This work has demonstrated that dithienoarsole is a promising building block for luminescent materials.
引用
收藏
页码:11338 / 11345
页数:8
相关论文
共 50 条
  • [41] Nonfullerene Acceptor for Organic Solar Cells with Chlorination on Dithieno[3,2-b:2′,3′-d]pyrrol Fused-Ring
    Geng, Renyong
    Song, Xin
    Feng, Haohao
    Yu, Jiangsheng
    Zhang, Ming
    Gasparini, Nicola
    Zhang, Zhuohan
    Liu, Feng
    Baran, Derya
    Tang, Weihua
    [J]. ACS ENERGY LETTERS, 2019, 4 (03) : 763 - 770
  • [42] Improvement of the redox stability of dithieno[3,2-b:2′,3′-d]thiophene derivatives by using bulky substituents
    Okada, Shinjiro
    Yamada, Kenji
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2013, 1037 : 256 - 263
  • [43] Design and photovoltaic characterization of dithieno[3,2-b:2′,3′-d]silole copolymers with positioning phenyl groups
    Zhu, Enwei
    Luo, Guoping
    Liu, Yun
    Yu, Jiangsheng
    Zhang, Fujun
    Che, Guangbo
    Wu, Hongbin
    Tang, Weihua
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2014, 16 (48) : 26893 - 26900
  • [44] Synthesis and photochromic reactivity of a new class of photochromic diarylethene dimer-containing dithieno[3,2-b:2′3′-d]thiophene
    Wang, Hongke
    Xu, Wei
    Zhu, Daoben
    [J]. TETRAHEDRON, 2012, 68 (42) : 8719 - 8723
  • [45] Synthesis and Photovoltaic Performance of Low Band Gap Dithieno[3,2-b:2′,3′-d]pyrrole-based Conjugated Copolymers
    Ren, Jing
    Chen, Wei-Ye
    Li, Feng
    Wang, Wei
    Yang, Ren-qiang
    Sun, Ming-liang
    [J]. ACTA POLYMERICA SINICA, 2018, (04): : 456 - 463
  • [46] Tuning the Photophysical Properties and Solid-State Organization of Perfluorophenyl-functionalized Dithieno[3,2-b:2′,3′-d]phospholes
    Dienes, Yvonne
    Englert, Ulli
    Baumgartner, Thomas
    [J]. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2009, 635 (02): : 238 - 244
  • [47] Synthesis of N-[4-Octylphenyl]dithieno[3,2-b:2′,3′-d]pyrrole-based broad absorbing polymers and their photovoltaic applications
    Tamilavan, Vellaiappillai
    Song, Myungkwan
    Kim, Sangjun
    Agneeswari, Rajalingam
    Kang, Jae-Wook
    Hyun, Myung Ho
    [J]. POLYMER, 2013, 54 (13) : 3198 - 3205
  • [48] N-Benzoyl dithieno[3,2-b:2′,3′-d]pyrrole-based hyperbranched polymers by direct arylation polymerization
    Tam Huu Nguyen
    Thu Anh Nguyen
    Hoan Minh Tran
    Nguyen, Le-Thu T.
    Anh Tuan Luu
    Lee, Jun Young
    Ha Tran Nguyen
    [J]. CHEMISTRY CENTRAL JOURNAL, 2017, 11
  • [49] Dithieno[3,2-b:2,3-d]arsole-containing conjugated polymers in organic photovoltaic devices
    Green, Joshua P.
    Cha, Hyojung
    Shahid, Munazza
    Creamer, Adam
    Durrant, James R.
    Heeney, Martin
    [J]. DALTON TRANSACTIONS, 2019, 48 (20) : 6676 - 6679
  • [50] Structure-Property Studies of Bichromophoric, PAH-Functionalized Dithieno[3,2-b:2′,3′-d]phospholes
    Chua, Chris Jansen
    Ren, Yi
    Baumgartner, Thomas
    [J]. ORGANOMETALLICS, 2012, 31 (06) : 2425 - 2436