2,5-dibromo-3-iodothiophene | 60404-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-dibromo-3-iodothiophene
• CAS: 60404-21-9
• 化学式: C₄HBr₂IS
• 分子量: 367.83
• InChiKey: OHKSAUNNMVWLRX-UHFFFAOYSA-N

物化性质

• 沸点：
  302.1±42.0 °C(Predicted)
• 密度：
  2.758±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-dibromo-3-iodothiophene 、 (4-ethynylphenyl)dimesitylborane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以51%的产率得到[4-[2-(2,5-Dibromothiophen-3-yl)ethynyl]phenyl]-bis(2,4,6-trimethylphenyl)borane
  参考文献：
  名称：

  Regioregular Organoborane-Functionalized Poly(3-alkynylthiophene)s

  摘要：

  In our quest to develop regioregular borane acceptor-modified thiophene polymers, we prepared a series of new alkynylphenylborane-functionalized monomers and explored their polymerization. The regioregular polymer rr-P1 and an alternating copolymer with 3-hexylthiopene, rr-P2, were successfully obtained by Stille-type polymerization. An X-ray crystal structure of the bithiophene model system 2-Br revealed coplanar thiophene rings and the formation of pi-stacks, despite the presence of bulky dimesitylborane moieties. For the polymers, rr-P1 showed the most bathochromic absorption (520 nm) and emission bands (620 nm), indicating the importance of high regioregularity and the beneficial effect of alkynyl relative to alkyl pendent groups. A higher energy absorption at ca. 340 nm could be assigned to charge transfer to the borane pendent groups based on DFT calculations on molecular model compounds that mimic the polymer repeat units. This assignment was further supported by fluoride anion binding studies.

  DOI：

  10.1021/ma501969q
• 作为产物：
  描述：

  3-碘噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙酸乙酯 为溶剂， 反应 30.0h， 以98%的产率得到2,5-dibromo-3-iodothiophene
  参考文献：
  名称：

  改进的合成基于噻吩基的单体配体，该配体形成用于还原二氧化碳的高活性聚合物

  摘要：

  背景：减少二氧化碳以获取重要的化学物质（例如燃料）是当前引起人们高度关注的话题。最近，设计了与联吡啶配体连接的单体噻吩和三噻吩，并且它们的聚合物薄膜在电催化CO2还原过程中实现了很高的周转率。在本文中，我们改进了访问表现出最佳性能的配体的方案，从而为获得侧官能化的对噻吩的通用方法开辟了道路。 方法：尝试了几种反应以改善合成途径。尝试了不同的方法将3-溴噻吩转化为其3-碘类似物并对其进行溴化以获得2,5-二溴-3-碘噻吩。通过使用Pd催化的交叉偶联反应（例如Sonogashira和Suzuki）来完成合成途径。尝试通过常规方法去除三甲基甲硅烷基保护基。但是，使用一锅法反应，炔烃脱保护和最终的Sonogashira偶联均作为获得最终产物的途径的关键。 结果：通过CuI辅助亲电子芳族取代，然后用NBS在乙酸乙酯中溴化，获得了关键中间体2,5-二溴-3-碘噻吩。该化合物与TMS-乙炔反应，得到（（2

  DOI：

  10.2174/1570178614666170503122330

文献信息

• Poly(alkynylthiophene)s and electronic devices generated therefrom
  申请人：Ong S. Beng

  公开号：US20070235719A1

  公开（公告）日：2007-10-11

  An electronic device comprising a semiconductive material of Formula wherein R is a suitable hydrocarbon or a heteroatom containing group; and n represents the number of repeating units.

  一种电子设备，包括具有以下结构的半导体材料：式中R是适当的碳氢化合物或含杂原子的基团；n代表重复单元的数量。
• Poly(alkynylthiophenes)s
  申请人：Ong S. Beng

  公开号：US20070238852A1

  公开（公告）日：2007-10-11

  A polymer of the following formula wherein R is a suitable hydrocarbon or a heteroatom containing group; and n represents the number of repeating units.

  以下是该聚合物的化学式，其中R是适当的碳氢化合物或含有杂原子的基团；n表示重复单元的数量。
• Poly(alkynylthiophene)s
  申请人：Xerox Corporation

  公开号：US07705111B2

  公开（公告）日：2010-04-27

  A polymer of the following formula wherein R is a suitable hydrocarbon or a heteroatom containing group; and n represents the number of repeating units.

  以下为化学式，其中R代表适当的碳氢或含杂原子的基团；n代表重复单元的数量。
• Impact of Pendant 1,2,3-Triazole on the Synthesis and Properties of Thiophene-Based Polymers
  作者：G. Nagarjuna、Serkan Yurt、Kedar G. Jadhav、D. Venkataraman

  DOI：10.1021/ma101657e

  日期：2010.10.12

  pi-Conjugated moieties are often attached to conjugated polymers to systematically alter their electronic properties. Herein, we report the synthesis and properties of a thiophene polymer hearing a triazole moiety in the third position. Through NMR-based quenching studies, we show that the placement of the triazole moiety alters reaction pathway of the Ni(0)-mediated Grignard metathesis polymerization possibly through chelation. When compared with a triazole on the main chain, the pendant triazole moiety acts as in electron donor and lowers the band gap of the polymer. The triazole moiety also does not hinder the packing of the conjugated backbone. We also show that the fluorescence of this polymer is quenched with PCBM. indicating its potential as a candidate or organic photovoltaic devices.
• Synthesis, Structures, and Hydroboration of Oligo- and Poly(3-alkynylthiophene)s
  作者：Frank Pammer、Fang Guo、Roger A. Lalancette、Frieder Jäkle

  DOI：10.1021/ma3010718

  日期：2012.8.28

  3-Alkynyl-substituted terthiophenes and polythiophenes were synthesized, and their properties and behavior toward hydroboration with Mes(2)BH were investigated. The alkynyl-substituted terthiophene was found to crystallize in an intriguing layered structure that mimics an interdigitated polymer wherein the terthiophenes form tightly pi-stacked linear pseudopolymer strands. The heptynyl side chains of neighboring stacks interlock ideally, almost completely filling the void in-between substituents and thus allowing for minimal spacing between neighboring pseudopolymer strands. Poly(3-alkynylthiophene)s were accessed through Grignard metathesis polymerization (GRIM) of 2,5-dibromo-3-heptynylthiophene, which yielded polymers of moderate molecular weights (M-n = 6.3; PDI = 1.73) in yields of up to 82%. Further modification by hydroboration with Mes2BH resulted in a material that is partially functionalized with vinylborane groups and as a result exhibits charge transfer bands in the UV-vis spectra. A single-crystal X-ray structure of the corresponding hydroborated terthiophene species shows extensive intermolecular interactions, resulting in pi-stacks of pi-dimers, despite the steric bulk of the dimesitylborane moieties.