3,3''-Dimethoxy-2,2':5',2''-terthiophene | 170662-12-1

• 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: 3,3''-Dimethoxy-2,2':5',2''-terthiophene
• 英文别名: 2,5-Bis(3-methoxythiophen-2-yl)thiophene
• CAS: 170662-12-1
• 化学式: C₁₄H₁₂O₂S₃
• 分子量: 308.446
• InChiKey: FWCLDCNJEIXIOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3''-Dimethoxy-2,2':5',2''-terthiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 5-tri(n-butyl)stannyl -3,3''-dimethoxy-5''-methyl -2,2':5',2''-terthiophene
  参考文献：
  名称：

  Oxidation of Unsymmetrically Substituted Quaterthiophene with Two Terminal Ferrocenyl Groups

  摘要：

  制备了具有两个末端二茂铁基的不对称取代的四噻吩作为长π-共轭体系。进行电化学和光谱研究以评估两个终端之间的电子和/或静电通信。由于低聚噻吩部分的不对称性，单电子氧化将发生在指定的一个二茂铁部分。延伸到低聚噻吩部分的单电子氧化物质显然与另一个末端二茂铁部分相互作用。

  DOI：

  10.1246/cl.2009.924
• 作为产物：
  描述：

  3-甲氧基噻吩 在 四(三苯基膦)钯 、 碘 、 mercury(II) oxide 作用下， 以 甲苯 、 苯 为溶剂， 反应 0.5h， 生成 3,3''-Dimethoxy-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Synthesis of .beta.-Methoxy, Methyl-Capped .alpha.-Oligothiophenes

  摘要：

  The first syntheses of structurally defined methoxyoligothiophenes are described. Nine alpha-coupled oligothiophenes, dimers through hexamers, symmetrically substituted at the ''inside'' or ''outside'' beta-positions with two or four methoxy groups, and with terminal methyl groups, were prepared. The electron-donor methoxy groups and terminal methyls have been shown to stabilize cationic species formed by oxidation or protonation of these oligomers. The oligomers were built up by the cross coupling of(mono- or oligo-) beta-methoxy-alpha-iodothiophenes and (mono- or oligo-) alpha-stannylthiophenes catalyzed by Pd(0)/Pd(ll) or by the redox home-coupling of alpha-thienyllithium compounds with Fe(acac)(3). Synthesis by the cross coupling of thienyl Grignard reagents and bromothiophenes with Ni(0) or Suzuki coupling using organoboranes was not successful. An X-ray crystal structure of a dimethoxy quaterthiophene is reported.

  DOI：

  10.1021/jo00126a034

文献信息

• Spectra and Reactivity of Methoxyoligothiophene Cation Radicals
  作者：Yuan Yu、Esmir Gunic、Baruch Zinger、Larry L. Miller

  DOI：10.1021/ja9533104

  日期：1996.1.1

  stable cation radicals. The E0 values for the reversible couples were 0.24−0.52 V (SCE). The changes in E0 with structure were explained using PPP molecular orbital calculations. Cation radicals were generated using either chemical or electrochemical oxidation, and in several cases stable salts were isolated. The vis−near-IR spectra of the cation radicals were recorded. In CH2Cl2 solvent the cation radicals

  研究了一组 α-偶联的低聚噻吩，二聚体到六聚体。每个低聚物以两个甲基封端并被两个或四个甲氧基取代。电化学研究表明，在末端环上的“内部”β-位（朝向链中心的位置）取代的甲氧基会产生稳定的阳离子自由基。可逆电偶的 E0 值为 0.24-0.52 V (SCE)。使用 PPP 分子轨道计算解释了 E0 随结构的变化。阳离子自由基是通过化学或电化学氧化产生的，在一些情况下，稳定的盐被分离出来。记录了阳离子自由基的可见近红外光谱。在 CH2Cl2 溶剂中，阳离子自由基是单体的，并显示出两个 π-π* 带，随着低聚物长度向更长的波长移动。在 CH3CN 溶剂中，阳离子自由基主要以 π-二聚体的形式存在，在近红外波段显示出两个 π-π* 带和一个电荷转移带。所有的...
• Direct C–H arylation of 3-methoxythiophene catalyzed by Pd. Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives
  作者：A. Borghese、G. Geldhof、L. Antoine

  DOI：10.1016/j.tetlet.2006.10.130

  日期：2006.12

  The direct regioselective C-H arylation of 3-methoxythiophene and 3,4-ethylenedioxythiophene (EDOT) was performed successfully under 'Heck-type' experimental conditions. This novel synthetic methodology has been used to prepare in a more simple way a series of oligothiophenes interesting for the electronic industry to build new synthetic organic materials. (c) 2006 Elsevier Ltd. All rights reserved.
• US5098529A
  申请人：——

  公开号：US5098529A

  公开（公告）日：1992-03-24
• Synthesis of .beta.-Methoxy, Methyl-Capped .alpha.-Oligothiophenes
  作者：Larry L. Miller、Yuan Yu

  DOI：10.1021/jo00126a034

  日期：1995.10

  The first syntheses of structurally defined methoxyoligothiophenes are described. Nine alpha-coupled oligothiophenes, dimers through hexamers, symmetrically substituted at the ''inside'' or ''outside'' beta-positions with two or four methoxy groups, and with terminal methyl groups, were prepared. The electron-donor methoxy groups and terminal methyls have been shown to stabilize cationic species formed by oxidation or protonation of these oligomers. The oligomers were built up by the cross coupling of(mono- or oligo-) beta-methoxy-alpha-iodothiophenes and (mono- or oligo-) alpha-stannylthiophenes catalyzed by Pd(0)/Pd(ll) or by the redox home-coupling of alpha-thienyllithium compounds with Fe(acac)(3). Synthesis by the cross coupling of thienyl Grignard reagents and bromothiophenes with Ni(0) or Suzuki coupling using organoboranes was not successful. An X-ray crystal structure of a dimethoxy quaterthiophene is reported.
• Oxidation of Unsymmetrically Substituted Quaterthiophene with Two Terminal Ferrocenyl Groups
  作者：Masa-aki Sato、Hirokazu Kamine

  DOI：10.1246/cl.2009.924

  日期：2009.9.5

  An unsymmetrically substituted quaterthiophene with two terminal ferrocenyl groups was prepared as a long π-conjugated system. Electrochemical and spectroscopic studies were carried out to evaluate the electronic and/or electrostatic communication between the two terminals. The one-electron oxidation would occur at one ferrocene moiety specified due to the unsymmetry of the oligothiophene moiety. The one-electron oxidizing species extended into the oligothiophene moiety apparently interacts with the other terminal ferrocene moiety.

  制备了具有两个末端二茂铁基的不对称取代的四噻吩作为长π-共轭体系。进行电化学和光谱研究以评估两个终端之间的电子和/或静电通信。由于低聚噻吩部分的不对称性，单电子氧化将发生在指定的一个二茂铁部分。延伸到低聚噻吩部分的单电子氧化物质显然与另一个末端二茂铁部分相互作用。