3'-(2-hydroxyethyl)-2,2':5',2''-terthiophene | 273400-09-2

• 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'-(2-hydroxyethyl)-2,2':5',2''-terthiophene
• 英文别名: 2-(2,5-Di(thiophen-2-yl)thiophen-3-yl)ethanol；2-(2,5-dithiophen-2-ylthiophen-3-yl)ethanol
• CAS: 273400-09-2
• 化学式: C₁₄H₁₂OS₃
• 分子量: 292.447
• InChiKey: PKEQYOPXZCPXEL-UHFFFAOYSA-N

物化性质

• 沸点：
  437.7±45.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 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：
  105
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-(2-hydroxyethyl)-2,2':5',2''-terthiophene 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以94%的产率得到3'-(2-bromoethyl)-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Nanotube Composites Consisting of Metal Nanoparticles and Polythiophene from Electropolymerization of Terthiophene-Functionalized Metal (Au, Pd) Nanoparticles

  摘要：

  We have developed a new method for the fabrication of metal nanoparticle/polythiophene nanotube composites, i.e., the template-based electrochemical polymerization of terthiophene-linked oligoethyleneoxy-thiol (1) and -phosphine (2)-stabilized gold and palladium nanoparticles (1-Au, 1-Pd, and 2-Pd) in a nanoporous alumina membrane as a template gave the nanotube composites (1-Au-PT-NTs, 1-Pd-PT-NTs, and 2-Pd-PT-NTs) of polythiophene and the metal nanoparticles without aggregation of the metal nanoparticles. The nanotube composites were characterized by scanning electron microscopy and transmission electron microscopy. The Pd/polythiophene nanotube composites (2-Pd-PT-NTs) are recyclable highly effective catalysts for carbon-carbon coupling reactions. This new method is currently being extended to other metal and metal oxide nanoparticles/polythiophene nanotube composites to realize a wide range of hybrid nanomaterials with controllable surface chemistry.

  DOI：

  10.1021/ja7114212
• 作为产物：
  描述：

  噻吩-3-乙酸乙酯 在 lithium aluminium tetrahydride 、 溴 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 3'-(2-hydroxyethyl)-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Electropolymerized and polymer grafted superhydrophobic, superoleophilic, and hemi-wicking coatings

  摘要：

  报告采用了一种新颖的一步法制造超疏水性和超亲油性电沉积涂层。通过对涂层进行额外的表面引发原子转移自由基聚合（SI-ATPR），观察到基底对各种液体的润湿性发生了进一步变化。

  DOI：

  10.1039/c2jm31067h

文献信息

• Surface-Initiated Ring-Opening Metathesis Polymerization (SI-ROMP): Synthesis and Electropolymerization of Terthiophene-Functionalized Olefin Peripheral Dendrons
  作者：Guoqian Jiang、Ramakrishna Ponnapati、Roderick Pernites、Mary Jane Felipe、Rigoberto Advincula

  DOI：10.1021/ma101746e

  日期：2010.12.28

  We report on the synthesis and electrodeposition of peripheral olefin dendrons with electropolymerizable focal point terthiophene units. These films were utilized for surface initiated ring-opening metathesis polymerization (SI-ROMP) of norbornene to form grafted polynorbornene brushes. The dendrons were first electrodeposited on an electrode surface, forming a highly dense and uniform polythiophene-type

  我们报告了具有可电聚合焦点对噻吩单元的外围烯烃树枝状分子的合成和电沉积。这些膜用于降冰片烯的表面引发的开环复分解聚合（SI-ROMP），以形成接枝的聚降冰片烯刷。首先将树枝状分子电沉积在电极表面上，形成高度致密且均匀的聚噻吩型薄膜，并研究其电化学行为。随后，在用过渡金属复分解催化剂活化后，从电沉积膜中生长出聚降冰片烯刷，发现该膜高度依赖于暴露的烯烃官能团的密度和树枝状分子的生成。通过原子力显微镜（AFM）检查了膜形态的变化。X射线光电子能谱（XPS）用于证明聚降冰片烯刷膜在电聚合层顶部的生长和组成。还进行了刷子生长动力学实验，以了解树枝状结构与聚降冰片烯刷子生长机理之间的相关性。本文提出的方法提供了一种简便的方法，可以制备从下面的π共轭聚合物层接枝的坚固，均匀且可控的聚合物刷。
• Electropolymerizable Terthiophene-Terminated Poly(aryl ether) Dendrimers with Naphthalene and Perylene Cores
  作者：Ramakrishna Ponnapati、Mary Jane Felipe、Rigoberto Advincula

  DOI：10.1021/ma201733a

  日期：2011.10.11

  terthiophene and n-type perylene and naphthalene diimides into one molecule, we have achieved a dual electrochromic material. These dendrimers were designed to act as electrochemically active precursor polymers, which bear the electroactive terthiophene group that can be cross-linked electrochemically to form conjugated polymer network (CPN) films. Characterization of the optical and redox properties

  我们描述了具有供体和受体部分的一系列新的聚（芳基醚）树状大分子的合成和表征。通过将p型对噻吩和n型per和萘二酰亚胺结合到一个分子中，我们获得了一种双电致变色材料。这些树枝状聚合物被设计为充当具有电化学活性的前体聚合物，它们带有可以通过电化学方式交联形成共轭聚合物网络（CPN）膜的电活性三噻吩基团。光学和氧化还原性质的表征表明，可以在保留掺杂性质的情况下将供体和受体部分掺入同一分子中。通过电化学聚合制备的薄膜在p和n掺杂过程中均具有很高的活性，并已通过光谱电化学方法进行了研究。
• Terthiophene-Jacketed Poly(benzyl ether) Dendrimers: Sonication Synthesis, Electropolymerization, and Polythiophene Film Formation
  作者：Ramakrishna Ponnapati、Mary Jane Felipe、Jin Young Park、Jonathan Vargas、Rigoberto Advincula

  DOI：10.1021/ma1017023

  日期：2010.12.28

  GPC to confirm the chemical structure and macromolecular properties of the dendrimers. Spectroscopic studies of thin films made by electropolymerization of these materials show the role that the dendrimer structure plays in the UV−vis absorption and emission properties of a highly cross-linked conjugated polymer film compared to linear polymers. The distinction is more evident in their emission behavior

  我们报告了一系列聚（苄基醚）型对噻吩夹套的树枝状大分子的设计和合成。这些树枝状大分子被设计为前体大分子，其带有可通过电化学方法交联形成共轭聚合物网络（CPN）聚噻吩薄膜的电活性三噻吩基团。通过NMR，元素分析，MALDI-TOF和GPC进行表征，以确认树枝状聚合物的化学结构和大分子性质。通过这些材料的电聚合制备的薄膜的光谱研究表明，与线性聚合物相比，树枝状大分子结构在高度交联的共轭聚合物薄膜的紫外可见吸收和发射特性中发挥了作用。这种区别在它们的发射行为上更加明显。尤其进行了共聚研究，以研究更线性的π-共轭序列的形成及其对光谱性质的影响。结果表明分子间的交联得到改善，在光谱的可见光区域形成了更多的发射物种。这些材料的光谱电化学研究表明，薄膜具有高度可逆的电致变色行为。
• Syntheses and electro(co)polymerization of novel thiophene- and 2,2′:5′,2″-terthiophene-functionalized metal–tetraazamacrocycle complexes, and electrochemical and spectroelectrochemical characterization of the resulting polythiophenes
  作者：Simon J. Higgins、Thomas J. Pounds、Paul A. Christensen

  DOI：10.1039/b103284b

  日期：——

  We have prepared novel tetraazacyclotetradecane derivatives, functionalised at nitrogen with a pendant thiophene or oligothiophene group, for electropolymerisation. Square planar Ni(II) complexes of these ligands, [Ni(L)](ClO4)2, have been prepared, and their electropolymerisation has been examined. The terthiophene-bearing complex was electrooxidised in CH3CN–0.2 M Et4NBF4 to give soluble oligomers, which are likely to be the products of dimerisation (sexithiophenes). However, by employing a more positive potential limit, they are electropolymerised, to afford polythiophene films on indium-doped tin oxide (ITO)-coated glass or platinum electrodes, and the Ni(II)/Ni(III) wave is superimposed upon the polythiophene redox process. Attempts to isolate films of the dimerised terthiophene by the oxidation of neutral [NiCl2(L)] complexes in less polar media were unsuccessful. A polymer film could not be generated from the thiophene-bearing complex alone, even though a ‘spacer’ of five carbon atoms was incorporated between the thiophene and the bulky metal centre. However, copolymerisation with 3-methylthiophene successfully gave polythiophene copolymers incorporating the nickel(II) complex. In situ FTIR reflectance spectroelectrochemistry shows that in the early stages of film oxidation, the film behaves as a conventional polythiophene, but at higher potentials, the electronic band attributable to the transition from the valence band to the first intergap state undergoes some very unusual changes. Possible explanations for these are suggested.

  我们已经制备了新型的四氮环十四烷衍生物，在氮原子上用悬挂的噻吩或寡噻吩基团进行功能化，以便进行电聚合。已经制备了这些配体的方形平面镍(II)络合物 [Ni(L)](ClO4)2，并对其电聚合进行了研究。含有三噻吩的络合物在 CH3CN–0.2 M Et4NBF4 中被电氧化，生成可溶的寡聚物，这些聚物可能是二聚化的产物（六噻吩）。然而，通过采用更正的电位极限，它们被电聚合，形成了在掺铟锡氧化物（ITO）涂层玻璃或铂电极上的聚噻吩薄膜，并且镍(II)/镍(III)波与聚噻吩的氧还原过程重叠。通过在非极性介质中氧化中性 [NiCl2(L)] 络合物来分离二聚的三噻吩薄膜的尝试未能成功。即使在噻吩和大分子金属中心之间加入了五个碳原子的“间隔”基团，仍无法单独从含噻吩的络合物生成聚合物薄膜。然而，与 3-甲基噻吩的共聚合成功生成了含有镍(II)络合物的聚噻吩共聚物。原位 FTIR 反射光谱电化学显示，在薄膜氧化的早期阶段，该薄膜表现得像传统的聚噻吩，但在更高的电位下，归因于从价带到第一个禁带态的跃迁的电子带经历了一些非常不寻常的变化。对此可能的解释被提出。
• Redox-active π-conjugated polymer nanotubes with viologen for encapsulation and release of fluorescent dye in the nanospace
  作者：Keisuke Sato、Tsukasa Nakahodo、Hisashi Fujihara

  DOI：10.1039/c1cc13853g

  日期：——

  We report the encapsulation of negatively charged Au nanoparticles and anionic fluorescent (FL) dye in the inner cavity of redox-active cationic polymer nanotubes with viologen via electrostatic interaction and the release of the FL dye from the FL dye confined in the cavity of the polymer nanotubes by electrochemical and chemical reduction.

  我们报告了带负电荷的金纳米粒子和阴离子荧光（FL）染料通过静电作用封装在具有氧化还原活性的阳离子聚合物纳米管的内腔中，并通过电化学和化学还原作用从聚合物纳米管的内腔中释放出 FL 染料。