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

被引：11

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

页码：4126 / 4130

页数：5

共 37 条

[1] A convenient and improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene
Allared, F
Hellberg, J
Remonen, T
[J]. TETRAHEDRON LETTERS, 2002, 43 (08) : 1553 - 1554
[2] [Anonymous], ORG LETT
[3] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
Beletskaya, Irina P.
Ananikov, Valentine P.
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
[4] Processable Low-Bandgap Polymers for Photovoltaic Applications
Boudreault, Pierre-Luc T.
Najari, Ahmed
Leclerc, Mario
[J]. CHEMISTRY OF MATERIALS, 2011, 23 (03) : 456 - 469
[5] Organic semiconductors:: A theoretical characterization of the basic parameters governing charge transport
Brédas, JL
Calbert, JP
da Silva, DA
Cornil, J
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (09) : 5804 - 5809
[6] Solvent-Controlled Halo-Selective Selenylation of Aryl Halides Catalyzed by Cu(II) Supported on Al2O3. A General Protocol for the Synthesis of Unsymmetrical Organo Mono- and Bis-Selenides
Chatterjee, Tanmay
Ranu, Brindaban C.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) : 7145 - 7153
[7] One-pot [1+1+1] synthesis of dithieno[2,3-b:3′,2′-d]thiophene (DTT) and their functionalized derivatives for organic thin-film transistors
Chen, Ming-Chou
Chiang, Yen-Ju
Kim, Choongik
Guo, Yue-Jhih
Chen, Sheng-Yu
Liang, You-Jhih
Huang, Yu-Wen
Hu, Tarng-Shiang
Lee, Gene-Hsiang
Facchetti, Antonio
Marks, Tobin J.
[J]. CHEMICAL COMMUNICATIONS, 2009, (14) : 1846 - 1848
[8] Polymer-Fullerene Bulk-Heterojunction Solar Cells
Dennler, Gilles
Scharber, Markus C.
Brabec, Christoph J.
[J]. ADVANCED MATERIALS, 2009, 21 (13) : 1323 - 1338
[9] Favaretto L., 2001, CHEM MATER, V13, P4112
[10] Fichou D., 1999, Handbook of Oligo- and Polythiophenes

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