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
  • [21] Planar Heptathienoacenes Based on Unsymmetric Dithieno[3,2-b:3′,4′-d]thiophene: Synthesis and Photophysical Properties
    Liu, Qiuxin
    Gao, Xiuxiu
    Zhong, Hao
    Song, Jinsheng
    Wang, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18): : 8612 - 8616
  • [22] Synthesis and Photovoltaic Characterization of Dithieno[ 3,2-b: 2', 3'-d] thiophene-Derived Narrow-Bandgap Polymers
    Zhu, Enwei
    Ni, Bin
    Zhao, Baofeng
    Hai, Jiefeng
    Bian, Linyi
    Wu, Hongbin
    Tang, Weihua
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2014, 215 (03) : 227 - 234
  • [23] 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
  • [24] Improvement of the redox stability of dithieno[3,2-b:2′,3′-d]thiophene derivatives by using bulky substituents
    Okada, Shinjiro
    Yamada, Kenji
    JOURNAL OF MOLECULAR STRUCTURE, 2013, 1037 : 256 - 263
  • [25] Easily Reducible Materials from the Reactions of Diselenopheno[3,2-b:2′,3′-d]pyrrole and Dithieno[3,2-b:2′,3′-d]pyrrole with Tetracyanoethylene
    Getmanenko, Yulia A.
    Purcell, Thomas A.
    Hwang, Do Kyung
    Kippelen, Bernard
    Marder, Seth R.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (23): : 10931 - 10937
  • [26] AN EFFICIENT SYNTHESIS OF QUINONE DERIVATIVES OF THIENO[3,2-B]THIOPHENE AND THIENO[3,2-B]THIENO[2',3'-D]THIOPHENE AND THEIR SPECTRAL PROPERTIES
    MAZAKI, Y
    TAKIGUCHI, N
    KOBAYASHI, K
    CHEMISTRY LETTERS, 1991, (07) : 1117 - 1120
  • [27] Synthesis and Characterization of Bis[1]benzothieno[3,2-b:2′,3′-d]pyrroles: Quantitative Effects of Benzannulation on Dithieno[3,2-b:2′,3′-d]pyrroles
    Wolfe, Rylan M. W.
    Culver, Evan W.
    Rasmussen, Seth C.
    MOLECULES, 2018, 23 (09):
  • [28] Synthesis and Photovoltaic Properties of Poly(dithieno[3,2-b:2′,3′-d]germole) Derivatives
    Gendron, David
    Morin, Pierre-Olivier
    Berrouard, Philippe
    Allard, Nicolas
    Aich, Badrou Reda
    Garon, Christian N.
    Tao, Ye
    Leclerc, Mario
    MACROMOLECULES, 2011, 44 (18) : 7188 - 7193
  • [29] Synthesis and Characterization of Poly(Dithieno[3,2-b:2′,3′-d]pyrrole) Derivatives Containing Thiophene Moieties and Their Application to Organic Devices
    Jeong, Hyung-Gu
    Lim, Bogyu
    Na, Seok-In
    Baeg, Kang-Jun
    Kim, Juhwan
    Yun, Jin-Mun
    Kim, Dong-Yu
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2011, 212 (21) : 2308 - 2318
  • [30] 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
    TETRAHEDRON, 2012, 68 (42) : 8719 - 8723