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
  • [31] Planar β-linked oligothiophenes based on thieno[3,2-b]thiophene and dithieno[3,2-b,2′,3′-d]thiophene fused units
    San Miguel, Lidaris
    Matzger, Adam J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [32] Synthesis and Photovoltaic Properties of a Low-Band-Gap Copolymer of Dithieno[3,2-b:2′,3′-d]thiophene and Dithienylquinoxaline
    Patil, Abasaheb V.
    Lee, Woo-Hyung
    Lee, Eunwoo
    Kim, Kyuri
    Kang, In-Nam
    Lee, Soo-Hyoung
    MACROMOLECULES, 2011, 44 (06) : 1238 - 1241
  • [33] Versatile and Practical Design of Dithieno[3,2-b:2',3'-d]arsole Polymers
    Takahara, Chisa
    Nakamura, Masashi
    Aoyama, Yuto
    Yanagihara, Takumi
    Ito, Shunichiro
    Tanaka, Kazuo
    Imoto, Hiroaki
    Naka, Kensuke
    MACROMOLECULES, 2023, 56 (17) : 6758 - 6763
  • [34] 2,6-bis(trimethylsilylethynyl)dithieno[3,2-b:2′,3′-d]thiophene
    Khan, MS
    Ahrens, B
    Raithby, PR
    Teat, SJ
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1226 - O1228
  • [35] A Facile Synthesis of Low-Band-Gap Donor-Acceptor Copolymers Based on Dithieno[3,2-b:2′,3′-d]thiophene
    Ku, Sung-Yu
    Liman, Christopher D.
    Burke, Daniel J.
    Treat, Neil D.
    Cochran, Justin E.
    Amir, Elizabeth
    Perez, Louis A.
    Chabinyc, Michael L.
    Hawker, Craig J.
    MACROMOLECULES, 2011, 44 (24) : 9533 - 9538
  • [36] Dithieno[3,2-b:2′,3′-d]pyrrole-based materials: Synthesis and application to organic electronics
    Rasmussen, Seth C.
    Evenson, Sean J.
    PROGRESS IN POLYMER SCIENCE, 2013, 38 (12) : 1773 - 1804
  • [37] Synthesis and characterization of β,β′-dimethylated dithieno[3,2-b:2′,3′-d]pyrroles and their corresponding regioregular conducting electropolymers
    Fortsch, Sebastian
    Mena-Osteritz, Elena
    Baeuerle, Peter
    POLYMER CHEMISTRY, 2021, 12 (22) : 3332 - 3345
  • [38] Synthesis and unexpected reactivity of si-h functionalized Dithieno[3,2-b:2′,3′-d]phospholes
    Baumgartner, T
    Wilk, W
    ORGANIC LETTERS, 2006, 8 (03) : 503 - 506
  • [39] 4-Aryldithieno[3,2-b:2′,3′-d]arsoles: effects of the As-substituent on the structure, photophysical properties, and stability
    Takahara, Chisa
    Iwasaki, Suzuka
    Kihara, Hyota
    Miyake, Yusuke
    Imoto, Hiroaki
    Naka, Kensuke
    DALTON TRANSACTIONS, 2022, 51 (36) : 13734 - 13741
  • [40] Synthesis and Properties of a Conjugated Acceptor Material for Organic Solar Cells Based on Indacenobis(dithieno[3,2-b:2′,3′-d]pyran)
    Ke, Xin
    Meng, Ling-xian
    Wan, Xiang-jian
    Zhang, Xin
    Chang, Mei-jia
    Li, Chen-xi
    Chen, Yong-sheng
    ACTA POLYMERICA SINICA, 2020, 51 (02): : 148 - 157