CAS: 116971-11-0; 2,5-Dibromo-3-Hexylthiophene

该化合物是一种溴化的硫苯衍生物,广泛用作合成聚合聚合物和有机半导体的关键中间体,其二溴替代在2,5个位置上能够产生有效的交叉反应,如铃木或斯蒂尔结合,便利建造扩展的-合成系统.六氧基侧链会提高普通有机溶剂的溶性,改善薄膜应用的可处理性.这种化合物对于有机电子材料的开发特别宝贵,包括聚合太阳电池,外效晶体和发光二极管.其定义完善的结构和高再活性使它成为先进材料研究的可靠建筑块.

结构式图片

相似化合物

158956-23-1 178452-13-6 116971-10-9

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合成工艺路线路线简述

  • 合成目标产物 2,5-Dibromo-3-Hexylthiophene 主要起始原料 1-Bromohexane
  • (文献来源)合成步骤主要原料 1-Bromohexane
溴己烷置于n-溴代丁二酰亚胺(Nbs),1,2-双(二苯基膦)乙烷氯化镍,Lithium Bromide,锌体系中,用 四氢呋喃,N,N-二甲基甲酰胺 用作溶剂,化学反应 3.0H,反应生成2,5-二溴-3-己基噻吩
参考文献:一种高效,可靠的高反应性立克锌的制备方法
标题:一种高效,可靠的高反应性立克锌的制备方法
摘要:Rieke锌在有机化学中具有广泛的应用潜力,特别是在高度化学选择性的有机锌试剂的合成中.但是,由于制备方法相当不可靠,导致批次间差异很大,因此其使用受到了很大的限制.Rieke锌通常是通过使用化学计量的萘将锂与氯化锌还原而制得的.在我们手中,观测到反应的结果高度依赖于萘的来源和纯度等级.苯并噻吩的存在似乎对于避免锌颗粒的凝结至关重要,并且苯并噻吩的量对所得锌粉的物理性质和反应性具有很大的影响.因此,2)将苯并噻吩放入萘锂溶液(原位制备)中.以这种方式获得的rieke锌被成功地用于所谓的" Rieke方法"中以制备区域规则的聚(3-己基噻吩)(p3Ht).该新颖方法使得能够以可再现的方式制备rieke锌,这极大地促进了其在小分子和聚合物合成中的使用.
Doi:10.1002/adsc.201201077

海关参考信息

专利信息


专利号:US-7834106-B2
优先权日:2005-04-01
标题:Living synthesis of conducting polymers including regioregular polymers, polythiophenes, and block copolymers
发明人:MCCULLOUGH RICHARD D; SHEINA ELENA E; IOVU MIHAELA C
权利人:UNIV CARNEGIE MELLON
摘要:Regioregular poly(3-alkylthiophenes) and other polythiophenes can be prepared by living polymerization which have good solubility, processability and environmental stability. The polymerization method can afford regioregular poly(3-alkylthiophenes) in high yields. Kinetic study of polymerization revealed the living character of this process. The molecular weight of poly(3-alkylthiophenes) is a function of the molar ratio of the monomer to nickel initiator, and conducting polymers with relatively narrow molecular weight distribution (PDI<1.5) are now readily available. Sequential monomer addition resulted in new block copolymers containing different poly(3-alkylthiophene) segments, which further confirms the “livingnessâ€? of this system. Other synthetic methods can be used as well to conduct living polymerization. Blends and electronic devices can be prepared.

专利号:US-2014187716-A1
优先权日:2011-07-15
标 题:Process for the synthesis of conjugated polymers
发明人:JONES DAVID JOHN; WONG WING HO WALLACE; HOLMES ANDREW BRUCE; SEYLER HELGA
权利人:JONES DAVID JOHN; WONG WING HO WALLACE; HOLMES ANDREW BRUCE; SEYLER HELGA; UNIV MELBOURNE
摘要:Processes for the continuous production of conjugated polymers are disclosed. The processes provide excellent control over reaction parameters and are highly reproducible. The conjugated polymers find use in heterojunction devices.

专利号:US-8168745-B2
优先权日:2007-08-02
标 题:Process for the preparation of poly- and oligothiophenes on an industrial scale
发明人:HENNINGER BJOERN; RAUSCHER FRANK; MLECZKO LESLAW
权利人:HENNINGER BJOERN; RAUSCHER FRANK; MLECZKO LESLAW; BAYER TECHNOLOGY SERVICES GMBH
摘要:Process for industrial scale synthesis of poly- and oligothiophenes, which works in concentrated solution. In this process, a solution which comprises an organometallic thiophene reagent is added to a second solution which comprises a catalyst.

专利号:CA-2692673-A1
优先权日:2007-07-09
标题 :Process for the synthesis of oligo/polythiophenes by a 'one-pot' synthesis route

专利号:US-2006278867-A1
优先权日:2005-04-01
标 题 :Living synthesis of conducting polymers including regioregular polymers, polythiophenes, and block copolymers

专利号:US-8541541-B2
优先权日:2005-03-07
标题:Conductive block copolymers
发明人:SILVERMAN GARY S; MCANDREW THOMAS P; SCHMIDT SCOTT C; MOUNTZ DAVID A; AUBART MARK A; RODAK NICHOLAS J
权利人:SILVERMAN GARY S; MCANDREW THOMAS P; SCHMIDT SCOTT C; MOUNTZ DAVID A; AUBART MARK A; RODAK NICHOLAS J; ARKEMA INC
摘要:The invention relates to the synthesis of polythiophene (PAT) copolymers, and their use as conductive polymers in final applications. Specifically, copolymers of PAT with (meth)acrylates, or amides are useful as additives in blends of different polymer matrices in many commercial applications.
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合成参考文献


参考文献:10.3390/ijms11125027
摘要:Yamada I, Takagi K, Hayashi Y, Soga T, Shibata N, Toru T. Poly[(3-hexylthiophene)-block-(3-semifluoroalkylthiophene)] for polymer solar cells. Int J Mol Sci. 2010;11(12):5027–39.
参考文献:10.1186/s13065-018-0404-7|10.1186/s13065-018-0451-0
摘要:Rizwan K, Zubair M, Rasool N, Mahmood T, Ayub K, Alitheen NB, Aziz MNM, Akhtar MN, Nasim F, Bukhary SM, Ahmad VU, Rani M. Palladium(0) catalyzed Suzuki cross-coupling reaction of 2,5-dibromo-3-methylthiophene: selectivity, characterization, DFT studies and their biological evaluations. Chemistry Central Journal. 2018 May 04;12(1). doi: 10.1186/s13065-018-0404-7.
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