2,5-双(5-己基噻吩-2-基)噻吩 | 188917-41-1

• 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
• 中文名称: 2,5-双(5-己基噻吩-2-基)噻吩
• 中文别名: 5,5''-二己基-2,2'：5'，2''-对噻吩
• 英文名称: 5,5''-dihexyl-2,2':5',2''-terthiophene
• 英文别名: 2,5-bis(5-hexylthiophen-2-yl)thiophene
• CAS: 188917-41-1
• 化学式: C₂₄H₃₂S₃
• 分子量: 416.716
• InChiKey: FQKINULSLUQGRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-hexyl-2,2':5',2''-terthiophene	151271-42-0	C18H20S3	332.555
  ——	5-hexanoyl-2,2':5',2''-terthiophene	173198-21-5	C18H18OS3	346.538
  alpha-三联噻吩	2,2':5',2''-terthiophene	1081-34-1	C12H8S3	248.394

反应信息

• 作为产物：
  描述：

  alpha-三联噻吩 在 氢氧化钾 、 四氯化钛 、 一水合肼 作用下， 以 二氯甲烷 、 二乙二醇 为溶剂， 反应 22.0h， 生成 2,5-双(5-己基噻吩-2-基)噻吩
  参考文献：
  名称：

  Byron, David; Matharu, Avtar; Wilson, Robert, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 265, p. 61 - 76

  摘要：

  DOI：

文献信息

• Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Brønsted Acids
  作者：Jonathan P. Brand、Jérôme Waser

  DOI：10.1002/anie.201003179

  日期：——

  United we stand! Cooperative activation of the hypervalent‐iodine reagent TIPS‐EBX with a gold catalyst and a Brønsted acid allowed the first direct ethynylation of thiophenes at room temperature (see scheme; TFA=trifluoroacetic acid). The obtained ethynylthiophenes are important building blocks for organic dyes and electronic materials.

  团结就是力量！高价碘试剂TIPS-EBX与金催化剂和布朗斯台德酸的协同活化使噻吩在室温下首次直接乙炔化（参见方案； TFA =三氟乙酸）。所获得的乙炔基噻吩是有机染料和电子材料的重要组成部分。
• Practical One-step Synthesis of Symmetrical Liquid Crystalline Dialkyloligothiophenes for Molecular Electronic Applications
  作者：Julie Leroy、Jeremy Levin、Sergey Sergeyev、Yves Geerts

  DOI：10.1246/cl.2006.166

  日期：2006.2

  This communication describes extremely simple one-step synthesis of α,α′-dialkyloligothiophenes by the lithiation/alkylation of the corresponding commercially available oligothiophenes. Use of t-BuOK to enhance the reactivity of lithiated oligothiophene species towards alkyl halides is crucially important.

  这项通讯描述了一种通过对相应的商业可得的寡噻吩进行锂化/烷基化，极其简单的一步合成α,α′-双烷基寡噻吩的方法。使用t-BuOK来增强锂化寡噻吩对烷基卤化物的反应性是至关重要的。
• Comparison of Thiophene-Pyrrole Oligomers with Oligothiophenes: A Joint Experimental and Theoretical Investigation of Their Structural and Spectroscopic Properties
  作者：María Moreno Oliva、Ted M. Pappenfus、Jacob H. Melby、Kathryn M. Schwaderer、Jared C. Johnson、Kari A. McGee、Demetrio A. da Silva Filho、Jean-Luc Bredas、Juan Casado、Juan T. López Navarrete

  DOI：10.1002/chem.201000143

  日期：——

  series of mixed thiophene–pyrrole oligomers to investigate the electronic benefits arising from the combination of these two heterocycles. The oligomers are functionalized with several hexyl and aryl groups to improve both processability and chemical robustness. An analysis of their spectroscopic (absorption and emission), photophysical, electrochemical, solid state, and vibrational properties is performed

  我们准备了一系列新的噻吩-吡咯混合低聚物，以研究这两个杂环的组合产生的电子益处。该低聚物被几个己基和芳基官能化以改善可加工性和化学稳定性。结合量子化学计算，对它们的光谱（吸收和发射），光物理，电化学，固态和振动特性进行了分析。该分析提供了有关将这些材料用作有机半导体的相关信息。吡咯的高芳香性与噻吩的中等芳香性之间的平衡使我们能够解决共轭体系中这些杂环偶联的影响。数据是根据芳香性来解释的，
• Oligothiophene <i>S</i>,<i>S</i>-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes
  作者：G. Barbarella、L. Favaretto、G. Sotgiu、M. Zambianchi、L. Antolini、O. Pudova、A. Bongini

  DOI：10.1021/jo980507g

  日期：1998.8.1

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.
• [EN] SEMICONDUCTING COMPOUND FOR GAS SENSING<br/>[FR] COMPOSÉ SEMI-CONDUCTEUR POUR LE CAPTAGE DE GAZ
  申请人：UNIV BRUXELLES

  公开号：WO2012156500A1

  公开（公告）日：2012-11-22

  A compound of general formula (I), as well as organic field effect transistors and gas sensors comprising the same.