2-perfluorobutylthiophene | 96721-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-perfluorobutylthiophene
• 英文别名: 2-perfluoro-n-butylthiophene；2-(Nonafluorobutyl)thiophene；2-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)thiophene
• CAS: 96721-81-2
• 化学式: C₈H₃F₉S
• 分子量: 302.163
• InChiKey: KKXHYYMDJMMUQM-UHFFFAOYSA-N

物化性质

• 沸点：
  72 °C(Press: 56 Torr)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  三丁基氯化锡 、 2-perfluorobutylthiophene 在 lithium diisopropyl amide 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以58%的产率得到2-perfluorobutyl-5-tri-n-butylstannylthiophene
  参考文献：
  名称：

  Synthesis of Perfluoroalkyl End-Functionalized Poly(3-hexylthiophene) and the Effect of Fluorinated End Groups on Solar Cell Performance

  摘要：

  A series of well-defined perfluoroalkyl end-functionalized poly(3-hexylthiophenes) (P3HT) were synthesized by Stifle coupling of stannylated 2-perfluoralkylthiophene with the bromine end of P3HT. The length of the perfluoroalkyl end group was varied from -C4F13 to -C8F17. These polymers were fully characterized and tested in bulk heterojunction solar cells with phenyl-C-61-butyric acid methyl ester (PCBM) as the acceptor. Performance of the solar cells was highest for the unmodified P3HT and decreased as the length of the perfluoroalkyl end increased. The most affected device parameters were the short-circuit current density (J(sc)) and series resistance, pointing to lower charge carrier mobility and poor morphology as the cause for the lower performance. While the morphology of blends did not significantly change with perfluoroalkyl end modification, analysis of blended films by energy-filtered transmission electron microscopy (EF-TEM) revealed wider P3HT domains, consistent with the perfluorinated end groups segregating to the edge or exterior of P3HT domains, causing two domains to join. This study demonstrates that the perfluoroalkyl end group can be detrimental to polymer solar cell device performance, and further work toward understanding the interface between the donor and acceptor phases is required to fully understand this effect.

  DOI：

  10.1021/ma301397p
• 作为产物：
  描述：

  2-溴噻吩 、 全氟碘代丁烷 在 copper bronze 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以50%的产率得到2-perfluorobutylthiophene
  参考文献：
  名称：

  Synthesis of Perfluoroalkyl End-Functionalized Poly(3-hexylthiophene) and the Effect of Fluorinated End Groups on Solar Cell Performance

  摘要：

  A series of well-defined perfluoroalkyl end-functionalized poly(3-hexylthiophenes) (P3HT) were synthesized by Stifle coupling of stannylated 2-perfluoralkylthiophene with the bromine end of P3HT. The length of the perfluoroalkyl end group was varied from -C4F13 to -C8F17. These polymers were fully characterized and tested in bulk heterojunction solar cells with phenyl-C-61-butyric acid methyl ester (PCBM) as the acceptor. Performance of the solar cells was highest for the unmodified P3HT and decreased as the length of the perfluoroalkyl end increased. The most affected device parameters were the short-circuit current density (J(sc)) and series resistance, pointing to lower charge carrier mobility and poor morphology as the cause for the lower performance. While the morphology of blends did not significantly change with perfluoroalkyl end modification, analysis of blended films by energy-filtered transmission electron microscopy (EF-TEM) revealed wider P3HT domains, consistent with the perfluorinated end groups segregating to the edge or exterior of P3HT domains, causing two domains to join. This study demonstrates that the perfluoroalkyl end group can be detrimental to polymer solar cell device performance, and further work toward understanding the interface between the donor and acceptor phases is required to fully understand this effect.

  DOI：

  10.1021/ma301397p

文献信息

• Copper-Catalyzed Oxidative Perfluoroalkylation of Aryl Boronic Acids Using Perfluoroalkylzinc Reagents
  作者：Xifei Bao、Lihua Liu、Junlan Li、Shilu Fan

  DOI：10.1021/acs.joc.7b02557

  日期：2018.1.5

  An efficient and synthetically convenient method for copper-catalyzed cross-coupling of aryl boronic acids with perfluoroalkyl zinc reagents has been described. The reaction proceeds under mild reaction conditions with a high efficiency and broad substrate scope and provides a general access to perfluoroalkylated arenes, which are of interest in life and materials science.

  已经描述了用于铜催化的芳基硼酸与全氟烷基锌试剂的交叉偶联的有效且合成方便的方法。该反应在温和的反应条件下进行，具有较高的效率和广泛的底物范围，并提供了进入全氟烷基化芳烃的一般途径，这是生命科学和材料科学中关注的问题。
• New Methods of Free-Radical Perfluoroalkylation of Aromatics and Alkenes. Absolute Rate Constants and Partial Rate Factors for the Homolytic Aromatic Substitution by <i>n</i>-Perfluorobutyl Radical
  作者：Anna Bravo、Hans-René Bjørsvik、Francesca Fontana、Lucia Liguori、Andrea Mele、Francesco Minisci

  DOI：10.1021/jo970302s

  日期：1997.10.1

  n-C(4)F(9)I has been utilized as source of C(4)F(9)(*) radical through iodine abstraction by phenyl or methyl radical. The reaction with alkenes, carried out in the presence of catalytic amount of Cu(OAc)(2), leads to substitution by a mechanism substantially identical to the aromatic substitution and not to the usual chain addition of perfluoroalkyl group and iodine atom to the double bond. This has

  报道了芳族化合物和烯烃的自由基全氟烷基化的新方法。nC（4）F（9）I已被用作C（4）F（9）（*）自由基的来源，通过苯基或甲基使碘抽象化。在催化量的Cu（OAc）（2）的存在下与烯烃的反应导致取代反应的机理基本上与芳族取代相同，并且不引起通常的全氟烷基和碘原子链加成到双链上键。这允许通过竞争动力学首次测量均相芳族全氟烷基化反应的绝对速率常数和部分速率因子。C（4）F（9）（*）自由基在芳族取代中显示出清晰的亲电特性，正如已经报道的向烯烃中的加成反应一样，但是低的区域选择性和化学选择性表明极性效应不是决定全氟烷基自由基对芳族化合物高反应性的主要因素（10（5）-10（6）M（-1）s（-1），2-活性比烷基高3个数量级。与所涉及的键能有关的焓因子似乎是反应性增加的主要原因。认为极性效应与可极化性的关系大于与自由基的极性（与π自由基相比，σ-全氟烷基自由基的极化性较小，因此对极性效应的敏感性
• Copper-mediated perfluoroalkylation of halogenothiophenes
  作者：J. Leroy、M. Rubinstein、C. Wakselman

  DOI：10.1016/s0022-1139(00)81309-3

  日期：1985.3
• LEROY, J.;RUBINSTEIN, M.;WAKSELMAN, C., J. FLUOR. CHEM., 1985, 27, N 3, 291-298
  作者：LEROY, J.、RUBINSTEIN, M.、WAKSELMAN, C.

  DOI：——

  日期：——
• Synthesis of Perfluoroalkyl End-Functionalized Poly(3-hexylthiophene) and the Effect of Fluorinated End Groups on Solar Cell Performance
  作者：Zhenghao Mao、Kiarash Vakhshouri、Cherno Jaye、Daniel A. Fischer、Roshan Fernando、Dean M. DeLongchamp、Enrique D. Gomez、Geneviève Sauvé

  DOI：10.1021/ma301397p

  日期：2013.1.8

  A series of well-defined perfluoroalkyl end-functionalized poly(3-hexylthiophenes) (P3HT) were synthesized by Stifle coupling of stannylated 2-perfluoralkylthiophene with the bromine end of P3HT. The length of the perfluoroalkyl end group was varied from -C4F13 to -C8F17. These polymers were fully characterized and tested in bulk heterojunction solar cells with phenyl-C-61-butyric acid methyl ester (PCBM) as the acceptor. Performance of the solar cells was highest for the unmodified P3HT and decreased as the length of the perfluoroalkyl end increased. The most affected device parameters were the short-circuit current density (J(sc)) and series resistance, pointing to lower charge carrier mobility and poor morphology as the cause for the lower performance. While the morphology of blends did not significantly change with perfluoroalkyl end modification, analysis of blended films by energy-filtered transmission electron microscopy (EF-TEM) revealed wider P3HT domains, consistent with the perfluorinated end groups segregating to the edge or exterior of P3HT domains, causing two domains to join. This study demonstrates that the perfluoroalkyl end group can be detrimental to polymer solar cell device performance, and further work toward understanding the interface between the donor and acceptor phases is required to fully understand this effect.