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
  • [1] A convenient and improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene
    Allared, F
    Hellberg, J
    Remonen, T
    TETRAHEDRON LETTERS, 2002, 43 (08) : 1553 - 1554
  • [2] SYNTHESIS OF DITHIENO[3,2-b:2 ',3 '-d]THIOPHENE
    Frey, Joseph
    Proemmel, Steffen
    Armitage, Michael A.
    Holmes, Andrew B.
    ORGANIC SYNTHESES, 2006, 83 : 209 - +
  • [3] A convenient synthesis and physicochemical properties of diselenopheno[3,2-b:2′,3′-d]thiophenes
    Kim, Hyokwon
    Kim, Min Jeong
    Zong, Kyukwan
    JOURNAL OF MOLECULAR STRUCTURE, 2021, 1229
  • [4] Photochromism of diarylethenes containing dithieno[3,2-b:2′,3′-d]thiophene
    Wang, Hongke
    Xu, Wei
    Zhu, Daoben
    DYES AND PIGMENTS, 2013, 97 (02) : 303 - 310
  • [5] Supramolecular assemblies with dithieno[3,2-b;2′,3′-d]thiophenes and other conjugated thiophene-containing π-systems
    Peters, L
    Sano, T
    Morrison, JJ
    Feeder, N
    Holmes, AB
    Kraft, A
    SYNTHETIC METALS, 2001, 119 (1-3) : 175 - 176
  • [6] 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
    Porter, William W., III
    Matzger, Adam J.
    ORGANIC LETTERS, 2007, 9 (06) : 1005 - 1008
  • [7] NITRATION OF DITHIENO[3,2-B/3',2'-D]PYRIDINE AND DITHIENO[3,2-B/3',4'-D]PYRIDINE
    SZABO, KJ
    GRONOWITZ, S
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (02) : 561 - 562
  • [8] 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
  • [9] Improved synthesis of dithieno[3,2-b:2′,3′-d] thiophene (DTT) and derivatives for cross coupling
    Frey, J
    Bond, AD
    Holmes, AB
    CHEMICAL COMMUNICATIONS, 2002, (20) : 2424 - 2425
  • [10] 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