3-bromo-4-(phenylethynyl)thiophene | 198693-57-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-bromo-4-(phenylethynyl)thiophene
• 英文别名: 3-Bromo-4-(2-phenylethynyl)thiophene；3-bromo-4-(2-phenylethynyl)thiophene
• CAS: 198693-57-1
• 化学式: C₁₂H₇BrS
• 分子量: 263.158
• InChiKey: VNIWWAFTCQOUOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  3-bromo-4-(phenylethynyl)thiophene 在 sodium sulfide 、 copper(II) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以22%的产率得到2-phenylthieno[3,4-b]thiophene
  参考文献：
  名称：

  Thieno[3,4-b]thiophene Acceptors with Alkyl, Aryl, Perfluoroalkyl, and Perfluorophenyl Pendants for Donor–Acceptor Low Bandgap Polymers

  摘要：

  We report the design, synthesis, and characterization of a series of thieno[3,4-b]thiophene acceptor blocks with octyl (T8), phenyl (TP), perfluorooctyl (TF8), and perfluorophenyl (TFP) side groups. Their subsequent copolymerization with dithienylbenzodithiophene by direct arylation polymerization afforded novel low bandgap poly(thienothiophene-alt-dithienylbenzodithiophene) (PTB) polymers. The strongly electron with-drawing TF8 and TFP groups were shown to significantly lower both E-HOMO and E-LUMO levels and gave computed copolymer ground-to-excited state dipole changes (triangle mu(ge)) that were relatively higher than for the nonfluorinated analogues. These materials show favorably aligned energy levels relative to conventional fullerene-type acceptors, which should allow them to perform well in organic photovoltaics.

  DOI：

  10.1021/ma4019476
• 作为产物：
  描述：

  苯基溴乙炔 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3-bromo-4-(phenylethynyl)thiophene
  参考文献：
  名称：

  芳基乙炔基溴化锌的直接制备及其在交叉偶联反应中的应用

  摘要：

  已经开发了用于制备芳基乙炔基溴化锌的新型合成方案。如此获得的有机锌试剂已成功地用于随后的交叉偶联反应中，并与多种芳基卤化物以良好至极好的收率提供了相应的炔基化化合物。

  DOI：

  10.1016/j.tetlet.2017.07.020

文献信息

• Synthesis of polyphenylene derivatives by thermolysis of enediynes and dialkynylaromatic monomers
  作者：Jens A John、James M Tour

  DOI：10.1016/s0040-4020(97)00977-0

  日期：1997.11

  Described are the syntheses of substituted enediynes and dialkynylaromatics using Pd- or cross coupling procedures. The products were then thermalized to afford the corresponding poly(p-phenylene)s, poly(1,4-naphthalene)s, poly(benzo[c]thiophene)s, and poly(dibenzothiophene)s. Fifteen examples are provided that show the scope of the polymerization process based upon substituent patterns and cyclization

  描述了使用Pd-或交叉偶联方法的取代烯二炔和二炔炔衍生物的合成。然后将产物加热，得到相应的聚（对苯撑），聚（1,4-萘），聚（苯并[ c]]噻吩和聚（二苯并噻吩）。提供了十五个实例，其基于取代基图案和环化部分显示了聚合过程的范围。使用热重分析法证明了新衍生的聚合物具有极好的热回弹性。通常使用与聚合物重复单元结构相似的小分子的红外数据相关性来确定聚合物的结构。由GCMS分析的二聚中间体的自由基捕获进一步证实了所提出的机理路线。通过监测单体消耗程度相对于聚合物分子量来确定逐步增长的聚合方式。
• A facile protocol for copper‐free palladium‐catalyzed Sonogashira coupling in aqueous media
  作者：Da‐Young Jung、Soo Youl Park、Seung‐Hoi Kim

  DOI：10.1002/bkcs.12432

  日期：2022.1

  combination of a readily available palladium catalyst and an eco-friendly basic aqueous solution of room-temperature ionic liquid, choline hydroxide (ChOH), was used in a facile protocol alternative to the Sonogashira coupling reaction, alkynylation of aryl halides in the absence of a copper cocatalyst and an external base. The dual nature of ChOH to act as a base and a green solvent played a crucial role in

  容易获得的钯催化剂和环境友好的室温离子液体碱性水溶液氢氧化胆碱 (ChOH) 的组合被用于替代 Sonogashira 偶联反应的简便方案，即在不存在芳基卤化物的情况下进行炔基化铜助催化剂和外部碱。ChOH 作为碱和绿色溶剂的双重性质在催化循环中起着至关重要的作用。尽管反应结果很大程度上取决于底物，但偶联反应在确定的条件下有效地进行以形成 Csp  Csp2 键。
• Heterocyclic fused selenophene monomers
  申请人：AIR PRODUCTS AND CHEMICALS, INC.

  公开号：EP2210883A2

  公开（公告）日：2010-07-28

  A heterocyclic fused selenophenes and a method of making a heterocyclic fused selenophenes of formula (1): wherein X is Se, Y is S, R is a substituent group. The monomer being capable of polymerization to form an electrically conductive polymer or oligomer.

  一种杂环融合硒烷和一种制造式（1）杂环融合硒烷的方法： 其中 X 是 Se，Y 是 S，R 是取代基。该单体能够聚合形成导电聚合物或低聚物。
• Direct preparation of arylethynylzinc bromides and their application to cross-coupling reactions
  作者：Seong-Ryu Joo、Jong-Sung Kim、Seung-Hoi Kim

  DOI：10.1016/j.tetlet.2017.07.020

  日期：2017.8

  A novel synthetic protocol for the preparation of arylethynylzinc bromides has been developed. Thus-obtained organozinc reagents were successfully employed in the subsequent cross-coupling reactions with a broad range of aryl halides providing the corresponding alkynylated compounds in good to excellent yields.

  已经开发了用于制备芳基乙炔基溴化锌的新型合成方案。如此获得的有机锌试剂已成功地用于随后的交叉偶联反应中，并与多种芳基卤化物以良好至极好的收率提供了相应的炔基化化合物。
• Thieno[3,4-<i>b</i>]thiophene Acceptors with Alkyl, Aryl, Perfluoroalkyl, and Perfluorophenyl Pendants for Donor–Acceptor Low Bandgap Polymers
  作者：Patrick D. Homyak、Jonathan Tinkham、Paul M. Lahti、E. Bryan Coughlin

  DOI：10.1021/ma4019476

  日期：2013.11.26

  We report the design, synthesis, and characterization of a series of thieno[3,4-b]thiophene acceptor blocks with octyl (T8), phenyl (TP), perfluorooctyl (TF8), and perfluorophenyl (TFP) side groups. Their subsequent copolymerization with dithienylbenzodithiophene by direct arylation polymerization afforded novel low bandgap poly(thienothiophene-alt-dithienylbenzodithiophene) (PTB) polymers. The strongly electron with-drawing TF8 and TFP groups were shown to significantly lower both E-HOMO and E-LUMO levels and gave computed copolymer ground-to-excited state dipole changes (triangle mu(ge)) that were relatively higher than for the nonfluorinated analogues. These materials show favorably aligned energy levels relative to conventional fullerene-type acceptors, which should allow them to perform well in organic photovoltaics.