3-(ω-bromopentyl)thiophene | 125878-90-2

• 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: 3-(ω-bromopentyl)thiophene
• 英文别名: 3-(5-bromopentyl)thiophene
• CAS: 125878-90-2
• 化学式: C₉H₁₃BrS
• 分子量: 233.172
• InChiKey: SKXOPADQXQZOSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(ω-bromopentyl)thiophene 在 硫脲 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以62%的产率得到5-(thien-3-yl)pentane-1-thiol
  参考文献：
  名称：

  Synthesis of Novel Alkyl- and Aryl Sulfides and Thiols as Precursors for Self-Assembled Monolayers on Gold

  摘要：

  制备了一系列4-烷基-1-溴硫代苯，包括S-甲基2、S-叔丁基3、S-三苯甲基4、S-苄基5和S-硅乙氧甲基6取代基，并评估它们在金(111)表面形成由S-芳基吸附物组成的单层膜的能力。单层膜的形成是通过在吸附到金表面时选择性地水解去除保护硫官能团的烷基。还制备了具有可变碳链长度和外围噻吩基团的硫醇9, 10, 17, 18和23-26。

  DOI：

  10.1055/s-2004-831163
• 作为产物：
  描述：

  1-(5-bromopentyloxy)-4-methoxy-benzene 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 氢溴酸 、 乙酸酐 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 3-(ω-bromopentyl)thiophene
  参考文献：
  名称：

  Baeuerle, Peter; Wuerthner, Frank; Heid, Stephan, Angewandte Chemie, 1990, vol. 102, # 4, p. 414 - 415

  摘要：

  DOI：

文献信息

• Donor–acceptor polythiophene copolymers with tunable acceptor content for photoelectric conversion devices
  作者：Marinella Catellani、Silvia Luzzati、Natalia-O. Lupsac、Raniero Mendichi、Roberto Consonni、Antonino Famulari、Stefano Valdo Meille、Francesco Giacalone、José L. Segura、Nazario Martín

  DOI：10.1039/b311370a

  日期：——

  The synthesis and characterization of a new series of substituted polythiophenes containing an electron acceptor anthraquinone moiety in the side chain are reported. The acceptor molar content was varied by the co-polymerization of both alkylthiophene and thiophene bearing anthraquinone monomers in different ratios. NMR analysis shows a good correlation between the monomer feed composition at the beginning of the polymerization and the actual unit composition of the backbone. The conjugation length and the chemical composition of the copolymers as a function of the molecular weight have been studied by size exclusion chromatography. Small angle X-ray scattering and UV-Vis absorption spectra have been used to monitor the degree of order and chain organization in the solid state. The materials exhibit a lamellar organization, in which the anthraquinone units of neighboring side chains are also organized to some degree in layered structures parallel to the polythiophene main chains. The photoluminescence measurements in solution suggest that, upon photoexcitation of the polythiophene backbone, the anthraquinone moieties act as electron acceptors and the conjugated backbone as electron donor. The tunability of the donor–acceptor ratio and the morphology in the solid state make these photoactive copolymers interesting candidates for organic photoelectric conversion devices.

  报告了一系列新的取代聚噻吩的合成与表征，这些聚合物的侧链含有电子受体蒽醌部分。通过不同比例共同聚合烷基噻吩和含有蒽醌单体的噻吩，改变了受体的摩尔含量。NMR分析显示聚合初期单体投料组成和实际骨架单位组成之间存在良好的相关性。通过尺寸排斥色谱研究了共聚物的共轭长度和化学组成对分子量的依赖性。小角X射线散射和紫外-可见吸收光谱被用来监测固态中的有序程度和链组织。材料呈现层状组织，其中相邻侧链的蒽醌单元在一定程度上也以平行于聚噻吩主链的层状结构组织。溶液中的光致发光测量表明，在对聚噻吩主链进行光激发后，蒽醌部分作为电子受体，而共轭主链则作为电子供体。供体-受体比率的可调性以及固态中的形态使得这些光活性共聚物成为有机光电转换设备的有趣候选材料。
• 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。
• The Hydrolytic Activity of Copper(II) Complexes with 1,4,7-Triazacyclononane Derivatives for the Hydrolysis of Phosphate Diesters
  作者：Michaela Buziková、Robert Willimetz、Jan Kotek

  DOI：10.3390/molecules28227542

  日期：——

  including a wide series of novel derivatives bearing a thiazole or thiophene side group, with the potential to incorporate these derivatives into a polymeric material; some previously known/studied ligands were also synthesised for comparative purposes. The corresponding copper(II) complexes were prepared, and their ability to mediate the hydrolysis of phosphate ester bonds was studied via UV-Vis

  合成了一组取代的1,4,7-三氮杂环壬烷配体，包括一系列带有噻唑或噻吩侧基的新型衍生物，有可能将这些衍生物掺入聚合物材料中；为了比较目的，还合成了一些先前已知/研究的配体。制备了相应的铜（II）配合物，并使用双（对硝基苯基）磷酸酯作为模型底物，通过紫外-可见分光光度法研究了它们介导磷酸酯键水解的能力。与之前研究的系统相比，一些制备的复合物显示出磷酸酯水解的显着增强，这使得它们成为为此目的测试过的最有效的复合物。因此，这些新颖的、潜在的双功能系统可以为创造用于医疗器械的新型涂层材料提供可能性，从而防止生物膜的形成。
• Intertwined Lamello-Columnar Coassemblies in Liquid-Crystalline Side-Chain Π-Conjugated Polymers: Toward a New Class of Nanostructured Supramolecular Organic Semiconductors
  作者：Danli Zeng、Ibtissam Tahar-Djebbar、Yiming Xiao、Farid Kameche、Navaphun Kayunkid、Martin Brinkmann、Daniel Guillon、Benoît Heinrich、Bertrand Donnio、Dimitri A. Ivanov、Emmanuelle Lacaze、David Kreher、Fabrice Mathevet、André-Jean Attias

  DOI：10.1021/ma4020356

  日期：2014.3.11

  A set of liquid-crystalline polymeric systems, associating at once the regioregular polythiophene backbone and pending mesogenic triphenylenes, is reported. Two series, namely regular homopolymers and alternating copolymers, were prepared by adapting a Grignard metathesis-based methodology, allowing some of the relevant structural parameters to be sequentially and independently modified. The thermal and self-organization behaviors of these uncommon macromolecular systems were investigated by polarized-light optical microscopy, differential scanning calorimetry and temperature-dependent small-angle X-ray scattering. Most polymers self-organize into mesophases possessing intertwined lamello-columnar morphologies, resulting from the simultaneous coexistence of lamellar and columnar sublattices. The successful preparation of oriented thin films of several of these polymeric homologues allowed further investigations by atomic force microscopy, transmission electron microscopy, electron diffraction, and grazing-incidence SAXS, which provided a deeper insight of the intricate supramolecular organizational modes, including the complete elucidation of the structure of the lamello-columnar mesophases. This simple and versatile strategy provides a route to elaborate polymeric materials incorporating two intercalated separate pathways toward charge carrier transport, of paramount importance for future electronic and optoelectronic applications.
• Synthesis of Soluble Donor−Acceptor Double-Cable Polymers Based on Polythiophene and Tetracyanoanthraquinodimethane (TCAQ)
  作者：Francesco Giacalone、José L. Segura、Nazario Martín、Marinella Catellani、Silvia Luzzati、Natalia Lupsac

  DOI：10.1021/ol034324e

  日期：2003.5.1

  [GRAPHICS]Novel suitably functionalized tetracyanoanthraquinodimethane (TCAQ) derivatives covalently linked to thiophene moieties have been synthesized. The thiophene-based monomers have been chemically polymerized and copolymerized to yield new and soluble donor-acceptor double-cable polymers. The absorption and emission data reveal that the optical properties can be finely tuned by modifying the ratio of monomers in the copolymerization process.