A Convenient Synthesis of Dithieno[3,2-b:2′,3′-d]thiophenes from Thiophene

被引：10
|
作者：
Park, Kyung Hyun [1 ]
Park, Joon Bum [1 ]
Zong, Kyukwan [1 ]
机构：
[1] Chonbuk Natl Univ, Dept Chem Educ, Div Sci Educ, Inst Fus Sci, Jeonju 561756, Jeonbuk, South Korea
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 23期
关键词：
thiophene; oligothiophenes; double annulations; tetraiodothiophene; semiconductors; STACKED ORGANIC SEMICONDUCTOR; CATALYZED C-S; FUSED THIOPHENES; HIGH-PERFORMANCE; DERIVATIVES; MONO; DTT; BIS;
D O I：
10.1055/s-0035-1562531
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthetic method for dithieno[3,2-b:2',3'-d]thiophenes was developed. The approach involves three steps starting from thiophene: tetraiodation of thiophene, selective dialkynylations on the 2,5-positions of the tetraiodothiophene, and finally CuI/TMEDA catalyzed double annulations of 2,5-dialkynyl-3,4-diiodothiophenes by Na2S, to afford dithieno[3,2-b: 2', 3'-d] thiophene and its derivatives.
引用
收藏
页码：4126 / 4130
页数：5
相关论文
共 50 条
  • [31] Synthesis, characterization and sensing properties of donor-acceptor systems based Dithieno[3,2-b;2′,3′-d]thiophene and boron
    Ipek, Ozgecan Savlug
    Topal, Sebahat
    Ozturk, Turan
    DYES AND PIGMENTS, 2021, 192
  • [32] Synthesis, characterization and sensing properties of donor-acceptor systems based Dithieno[3,2-b;2′,3′-d]thiophene and boron
    Ipek, Ozgecan Savlug
    Topal, Sebahat
    Ozturk, Turan
    Ozturk, Turan (ozturktur@itu.edu.tr), 1600, Elsevier Ltd (192):
  • [33] Thiophene-dithieno[3,2-B:2′,3′-D]pyrrole mixed oligomers as precursors to new conjugated systems
    Radke, KR
    Ogawa, K
    Rasmussen, SC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U162 - U163
  • [34] Synthesis of new dithieno[3,2-b:2′,3′-d]pyrrole (DTP) units for photovoltaic cells
    Ge, Gaoyang
    Dai, Panpan
    Lu, Ziyi
    Liang, Mao
    Dong, Huanhuan
    Sun, Zhe
    Xue, Song
    DYES AND PIGMENTS, 2016, 128 : 8 - 18
  • [35] Synthesis and bioconjugation of first alkynylated poly(dithieno[3,2-b: 2′, 3′-d]pyrrole)s
    Schmid, Sylvia
    Gacanin, Jasmina
    Wu, Yuzhou
    Weil, Tanja
    Baeuerle, Peter
    POLYMER CHEMISTRY, 2017, 8 (46) : 7113 - 7118
  • [36] SYNTHESIS OF NEW 2-ARYLTHIENO[3,2-B]THIOPHENES
    PRIM, D
    KIRSCH, G
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18): : 2603 - 2606
  • [37] Synthesis of dithieno[3,2-b:2′3′-d]pyrrole-based poly(arylenevinylene) materials
    Hofsommer, Dillon T.
    Evenson, Sean J.
    Rasmussen, Seth C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [38] New methods for the synthesis of 4H-dithieno[3,2-b: 2', 3'-d] pyrrole
    Foertsch, Sebastian
    Vogt, Astrid
    Baeuerle, Peter
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2017, 30 (09)
  • [39] Improved synthesis of N-alkyl substituted dithieno[3,2-b:2′,3′-d]pyrroles
    Koeckelberghs, G
    De Cremer, L
    Vanormelingen, W
    Dehaen, W
    Verbiest, T
    Persoons, A
    Samyn, C
    TETRAHEDRON, 2005, 61 (03) : 687 - 691
  • [40] Synthesis of dithieno[3,2-b:2',3' d]pyrrole-based diarylethylenes as polymer precursors
    Evenson, Sean J.
    Wohl, Adam R.
    Rasmussen, Seth C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
12345