2,5-双(5-甲基噻吩-2-基)噻吩 | 59949-61-0

• 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
• 中文名称: 2,5-双(5-甲基噻吩-2-基)噻吩
• 英文名称: 5,5"-dimethyl-2,2':5',2"-terthiophene
• 英文别名: 2,2':5',2''-Terthiophene, 5,5''-dimethyl-；2,5-bis(5-methylthiophen-2-yl)thiophene
• CAS: 59949-61-0
• 化学式: C₁₄H₁₂S₃
• 分子量: 276.447
• InChiKey: UCLXUPRIAJUZED-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  369.0±37.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(η(5)-cyclopentadienyl)Os(acetonitrile)3]PF6 、 2,5-双(5-甲基噻吩-2-基)噻吩 以 丙酮 为溶剂， 以69%的产率得到[(cyclopentadienyl)Os(η(5)-5,5''-dimethyl-2,2':5'2''-terthiophene)]PF6
  参考文献：
  名称：

  Electrochemical Investigation of Ruthenium and Osmium Oligothiophene Complexes:  How Does Metal Binding Affect the Oligothiophene π-System?

  摘要：

  We have studied the electrochemistry of a series of oligothiophene complexes with one or more ''Cp*Ru+'' ''CpRu(+)'', or ''CpOs(+)'' fragments (Cp=cyclopentadienyl; Cp*=pentamethylcyclopentadienyl) attached to the oligothiophene pi-system. This series varies the metal (Ru or Os), ancillary ligand (Cp or Cp*), ring substituents (phenyl or methyl groups), and length of the oligothiophene (1-4 rings). The peak potentials for the oxidation of the free oligothiophenes and their complexes indicate that the electron hole produced upon oxidation of the complexes is delocalized on the uncomplexed rings of the oligothiophene. Oxidation of the complexes results in conductive films-on the electrode but the composition of the electrodeposited films is unclear. The electron added upon reduction of the complexes is localized on the [Cp/Cp*M(thiophene)](+) unit formed by complexation of the oligothiophene. We propose that complexation of a thiophene ring converts it into a [Cp/Cp*M(thiophene)](+) unit and removes it from conjugation with the remaining, uncomplexed rings. The unbound rings function as a shortened, metal-substituted oligothiophene unit. Complexation of oligothiophenes by "Cp*Ru+", "CpRu(+)", and "CpOs(+)" fragments is a rational method for controlling the properties of oligothiophenes.

  DOI：

  10.1021/ic960309c
• 作为产物：
  描述：

  2-乙炔基-5-甲基噻吩 在 sodium sulfide 、 air 、 四甲基乙二胺 、 copper(l) chloride 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 25.0h， 生成 2,5-双(5-甲基噻吩-2-基)噻吩
  参考文献：
  名称：

  Synthesis of 3,2':5',3"-terthiophene and other terthiophenes by the thiophenecarboxaldehyde .fwdarw. ethynylthiophene .fwdarw. dithienylbutadiyne route

  摘要：

  DOI：

  10.1021/jo00132a047

文献信息

• [EN] IMPROVED OLIGOTHIOPHENES<br/>[FR] OLIGOTHIOPHÈNES AMÉLIORÉS
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2011137487A1

  公开（公告）日：2011-11-10

  Compounds of Formula (I), wherein T is independently selected from the group consisting of (a). And the variables R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar, L and n are as defined in the specification herein. The compounds are capable of charge transportation and have application in organic photovoltaic devices such as dye sensitised solar cells.

  式（I）的化合物，其中T是从（a）组成的群体中独立选择的。变量R1、R2、R3、R4、R5、R6、R7、R8、R9、Ar、L和n的定义如本说明书中所述。这些化合物能够进行电荷传输，并在有机光伏器件中应用，例如染料敏化太阳能电池。
• Bithiophene Sulfonamide-Based Molecular and Polymeric Semiconductors
  申请人：Northwestern University

  公开号：US20160149138A1

  公开（公告）日：2016-05-26

  The present invention relates to new semiconducting compounds having at least one optionally substituted bithiophene sulfonamide moiety. The compounds disclosed herein can exhibit high carrier mobility and/or efficient light absorption/emission characteristics, and can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

  本发明涉及具有至少一个可选择取代的双噻吩磺酰胺基团的新半导体化合物。本文所披露的化合物可以表现出高载流子迁移率和/或高效的光吸收/发射特性，并且具有一定的加工优势，如可溶性加工性和/或在常温下良好的稳定性。
• ORGANIC SEMICONDUCTING COMPOUNDS AND RELATED OPTOELECTRONIC DEVICES
  申请人：Polyera Corporation

  公开号：US20170104160A1

  公开（公告）日：2017-04-13

  The present teachings relate to new organic semiconducting compounds and their use as active materials in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The present compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The present compounds can have good solubility in common solvents enabling device fabrication via solution processes.

  本教学涉及新的有机半导体化合物及其在有机和混合光学、光电子和/或电子器件中作为活性材料的用途，如光伏电池、发光二极管、发光晶体管和场效应晶体管。这些化合物可以提供改进的器件性能，例如通过光电转换效率、填充因子、开路电压、场效应迁移率、开/关电流比以及在光伏电池或晶体管中使用时的空气稳定性等指标来衡量。这些化合物在常见溶剂中具有良好的溶解性，可以通过溶液工艺进行器件制备。
• Approaching the Integer‐Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross‐Coupling
  作者：Jiang Tian Liu、Hannes Hase、Sarah Taylor、Ingo Salzmann、Pat Forgione

  DOI：10.1002/anie.201914458

  日期：2020.4.27

  A library of symmetrical linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach compared to the existing methods. The modularity

  使用脱羧交叉偶联反应作为关键转化制备了对称的线性低聚噻吩文库。噻吩羧酸钾盐用作交叉偶联伙伴，而无需助催化剂，碱或添加剂。与现有方法相比，该方法显示出完全的化学选择性，是一种更全面的绿色方法。通过制备具有最多10个噻吩重复单元的谨慎的寡聚噻吩，可以证明这种方法的模块化。对称的低聚噻吩是典型的有机半导体，可以通过光谱评估其分子电掺杂随链长的变化。观察到整数电荷转移的低聚噻吩临界长度为10个噻吩单元，
• Silver‐Catalysed Hydroarylation of Highly Substituted Styrenes
  作者：Toryn Dalton、Steffen Greßies、Mowpriya Das、Maximilian Niehues、Malte L. Schrader、Christian Gutheil、Bart Jan Ravoo、Frank Glorius

  DOI：10.1002/anie.202016268

  日期：2021.4.6

  Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three‐dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes, however most of these reports examine the hydroarylation of unpolar, β‐mono‐ or β‐unsubstituted styrenes, while exploring mainly electron‐rich benzene

  加氢芳基化是一种有效的策略，可通过将平面烯烃部分转化为三维框架来快速增加有机结构的复杂性。已经开发出许多策略来实现苯乙烯的加氢芳基化，然而，大多数这些报告在主要研究富含电子的苯亲核试剂的同时，研究了非极性，β-单取代或β-未取代的苯乙烯的加氢芳基化。在本文中，我们报道了一种温和而通用的催化体系，用于多取代苯乙烯和杂芳族苯乙烯的选择性加氢杂芳基化。反应的机理分析导致发现了市售的2,2'：5'，2''-噻吩作为关键试剂。