5,5'-bis(p-tolyl)-2,2'-bithiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-bis(p-tolyl)-2,2'-bithiophene
• 英文别名: 5,5'-di(4-methylphenyl)-2,2'-bithiophene；5,5'-di-p-tolyl-2,2'-bithiophene；5,5'-bis[4-methylphenyl]-2,2'-bithiophene；2-(4-Methylphenyl)-5-[5-(4-methylphenyl)thiophen-2-yl]thiophene
• 化学式: C₂₂H₁₈S₂
• 分子量: 346.517
• InChiKey: UIPHRRKDTBFJIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-噻吩-2-苯基)甲醇 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 氟化银 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以58%的产率得到5,5'-bis(p-tolyl)-2,2'-bithiophene
  参考文献：
  名称：

  Palladium-Catalyzed C−H Homocoupling of Thiophenes:  Facile Construction of Bithiophene Structure

  摘要：

  Palladium-catalyzed C-H homocoupling of thiophene derivatives takes place in the presence of silver(I) fluoride or acetate. A variety of bithiophenes are obtained in good to excellent yields. In particular, the reaction of 2-bromothiophene proceeds at room temperature to afford 5,5'-dibromo-2,2'-bithiophene, where the bromine atom is completely intact in the palladium-catalyzed reaction. XRD analysis reveals that silver fluoride is reduced to silver(0) during the reaction.

  DOI：

  10.1021/ja031855p

文献信息

• Direct C–H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex
  作者：Yabo Li、Jingran Wang、Mengmeng Huang、Zhiwei Wang、Yusheng Wu、Yangjie Wu

  DOI：10.1021/jo402745b

  日期：2014.4.4

  An efficient phosphine-free direct C–H arylation of thiophenes at the α-position has been developed at low catalyst loading of bis(alkoxo)palladium complex (Cat.I, 0.1–0.2 mol %). The developed synthetic method can be applied to the synthesis of α-aryl/heteroaryl thiophenes from aryl or heteroaryl bromides in good to excellent yields and is compatible with the substrates bearing electron-donating or

  在双（烷氧基）钯配合物（Cat.I，0.1-0.2 mol％）的低催化剂负载下，已开发出一种有效的无磷的噻吩在α位上无膦直接CH芳基化的化合物。所开发的合成方法可用于从芳基或杂芳基溴化物以良好至优异的产率合成α-芳基/杂芳基噻吩，并且与带有给电子或吸电子基团的底物相容。噻吩2位和5位的反应性是相同的，并且在最佳条件下不依赖于空间位阻。该条件还可以以高转化率应用于其他杂环部分，例如苯并噻吩，苯并呋喃和吡咯。
• Impact of terminal substituents on the electronic, vibrational and optical properties of thiophene–phenylene co-oligomers
  作者：Andrey Yu. Sosorev、Muzaffar K. Nuraliev、Elizaveta V. Feldman、Dmitry R. Maslennikov、Oleg V. Borshchev、Maxim S. Skorotetcky、Nikolay M. Surin、Maxim S. Kazantsev、Sergei A. Ponomarenko、Dmitry Yu. Paraschuk

  DOI：10.1039/c9cp00910h

  日期：——

  conjugation length of the substituted oligomer. A detailed picture underlying the effect of the terminal substituents on the electronic, vibrational and optical properties of TPCOs is presented. Overall, the unraveled relationships between the structure and the properties of the substituted PTTPs should facilitate a rational design of π-conjugated (co-)oligomers for efficient organic optoelectronic

  由于有效的电荷传输和明亮的发光相结合，噻吩-苯撑共聚体（TPCO）是用于有机发光器件（如二极管，晶体管和激光器）的有前途的材料。TPCO的综合灵活性使其特性的调整变得容易。在这项研究中，我们研究了各种给电子和吸电子对称末端取代基（氟，甲基，三氟甲基，甲氧基，叔-丁基和三甲基甲硅烷基），5,5'-联苯-2,2'-联噻吩（PTTP）的电荷，分布，静态极化率，分子振动，带隙和光致发光量子产率。通过将DFT计算与循环伏安法和吸收，光致发光和拉曼光谱相结合，我们发现对称末端取代可在约0.7 eV的范围内调节TPCO的最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）能量。改变与苯环相关的振动模式的频率，将光致发光量子产率改变约两倍，并将带隙略微改变约0.1 eV。我们证明这些影响受两个因素支配：取代基的哈米特常数及其在π-共轭/超共轭中的参与，用取代低聚物的有效共轭长度来描述。提供了详细的
• Synthesis of thiophene/phenylene co-oligomers. I. Phenyl-capped oligothiophenes
  作者：S. Hotta、S. A. Lee、T. Tamaki

  DOI：10.1002/jhet.5570370105

  日期：2000.1

  We report the synthesis of phenyl-capped oligothiophenes via improved synthetic schemes. These schemes are based on the Grignard coupling reaction and enable us to obtain the target compounds at high yields. The resulting materials have been fully characterized through nmr and ir spectroscopies. The ir analysis is particularly useful in characterizing the materials of higher molecular weight, since

  我们报告了通过改进的合成方案的苯基封端的寡噻吩的合成。这些方案基于格利雅偶联反应，使我们能够以高收率获得目标化合物。所得材料已通过核磁共振和红外光谱进行了充分表征。ir分析对于表征较高分子量的材料特别有用，因为这些材料难以溶解在有机溶剂中。我们还显示了对用作合成目标化合物中间体的卤代（低聚）噻吩的制备方法的改进。还提出了利用铃木偶联反应的苯基封端的低聚噻吩的另一种合成途径。
• COMPOUND HAVING TRIMETHYLENE STRUCTURE, POLYMER COMPOUND CONTAINING UNIT THAT HAS TRIMETHYLENE STRUCTURE, AND REACTIVE COMPOUND HAVING TRIMETHYLENE STRUCTURE
  申请人：Funyuu Shigeaki

  公开号：US20120289674A1

  公开（公告）日：2012-11-15

  A compound represented by a formula 1 shown below. In the formula 1, each of R1 and R2 independently represents a group selected from the group consisting of a hydrogen atom and substituents composed of C, H and/or X (wherein X represents a hetero atom), and each of Z1 and Z2 independently represents a group selected from the group consisting of aromatic substituents composed of C and H, aromatic substituents composed of C, H and X (wherein X represents a hetero atom), groups containing an aromatic ring and a double-bonded and/or triple-bonded conjugated structure composed of C and H, and groups containing an aromatic ring and a double-bonded and/or triple-bonded conjugated structure composed of C, H and/or X (wherein X represents a hetero atom).

  下面是公式1所代表的化合物。在公式1中，R1和R2中的每一个都独立地表示从由C、H和/或X（其中X表示杂原子）组成的取代基和氢原子组成的群中选择的群，而Z1和Z2中的每一个都独立地表示从由C和H组成的芳香基取代物、由C、H和X（其中X表示杂原子）组成的芳香基取代物、含有芳香环和双键和/或三键共轭结构的由C和H组成的基团以及含有芳香环和双键和/或三键共轭结构的由C、H和/或X（其中X表示杂原子）组成的基团中选择的群。
• DYE FOR DYE-SENSITIZED SOLAR CELL, SEMICONDUCTOR ELECTRODE, AND DYE-SENSITIZED SOLAR CELL
  申请人：Mitsubishi Paper Mills Limited

  公开号：EP2309584A1

  公开（公告）日：2011-04-13

  The dye for a dye-sensitized solar cell, which dye is a compound classified into melocyanine dyes and has a structure in which an electron donor unit and an electron acceptor unit are connected with conjugated double bonds, provided by this invention, has excellent photoelectric conversion efficiency and excellent durability, and according to this invention, there can be provided a semiconductor electrode sensitized by the dye and a dye-sensitized solar cell using the semiconductor electrode.

  本发明提供的用于染料敏化太阳能电池的染料是一种化合物，属于三聚氰胺染料，具有电子供体单元和电子受体单元用共轭双键连接的结构，具有优异的光电转换效率和出色的耐久性，根据本发明，可以提供由该染料敏化的半导体电极和使用该半导体电极的染料敏化太阳能电池。