5,5'''-二己基-2,2':5',2'':5'',2'''-四噻吩 | 132814-92-7

• 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: 5,5'''-二己基-2,2':5',2'':5'',2'''-四噻吩
• 中文别名: Α,Ω-二己基四噻吩
• 英文名称: α,ω-dihexylquaterthiophene
• 英文别名: 5,5'''-dihexyl-2,2':5',2'':5'',2'''-quaterthiophene；2-hexyl-5-[5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene
• CAS: 132814-92-7
• 化学式: C₂₈H₃₄S₄
• 分子量: 498.842
• InChiKey: KGJQHEPGNCWZRN-UHFFFAOYSA-N

物化性质

• 熔点：
  178.0 to 182.0 °C
• 沸点：
  569.6±45.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)
• 最大波长(λmax)：
  402nm(THF)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

反应信息

• 作为产物：
  描述：

  2,2'-联二噻吩 在 正丁基锂 、 iron(II) acetylacetonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 5,5'''-二己基-2,2':5',2'':5'',2'''-四噻吩
  参考文献：
  名称：

  Oligothiophene S,S-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes

  摘要：

  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.

  DOI：

  10.1021/jo980507g

文献信息

• A Convoluted Polyvinylpyridine‐Palladium Catalyst for Suzuki‐Miyaura Coupling and C−H Arylation
  作者：Aya Ohno、Takuma Sato、Toshiaki Mase、Yasuhiro Uozumi、Yoichi M. A. Yamada

  DOI：10.1002/adsc.202000742

  日期：2020.11.4

  and reusable supported catalysts for Suzuki‐Miyaura coupling and catalytic C−H arylation is important for fundamental and applied chemistry, with these reactions being used to produce medical compounds and functional materials. Herein, we found that a mesoporous composite made of a linear poly(4‐vinylpyridine) and tetrachloropalladate acted as a dual‐mode catalyst for a variety of cross‐coupling reactions

  开发用于铃木-宫浦偶合和催化CH芳基化的高活性和可重复使用的载体催化剂对于基础化学和应用化学至关重要，这些反应可用于生产医药化合物和功能材料。在这里，我们发现由线性聚（4-乙烯基吡啶）和四氯钯酸盐制成的介孔复合物充当多种交叉偶联反应的双模催化剂，在不同条件下观察到Pd纳米颗粒和Pd络合物催化剂。聚乙烯基吡啶钯复合材料1通过聚（4-乙烯基吡啶）和四氯钯酸钠的分子卷积可轻松制备得到难溶的聚合物-金属复合材料。铃木-宫浦耦合和芳基氯，并用芳基硼酸，噻吩，呋喃，苯溴化物的C-H芳基化，和苯甲醚在0.004摩尔％（40摩尔ppm的）存在下进行，以1摩尔％的Pd的1，得到相应的偶联产品产量高。此外，催化剂可以重复使用而没有明显的活性损失。药物化合物和功能材料通过偶联反应合成。N 2气体吸附/解吸分析表明该催化剂具有介孔性质，在催化中起关键作用。在铃木宫浦联轴器中在聚合物基体中原位生成的钯纳米粒子具有催
• A new method of using supercritical carbon dioxide as a green solvent for synthesis and purification of 5,5‴-bis(tridecafluorohexyl)-2,2′:5′,2″:5″,2‴-quaterthiophene, which is one of n-type organic semiconducting materials
  作者：Ryuji Hirase、Koji Honda、Mari Ishihara、Hideki Yoshioka、Hirosato Monobe

  DOI：10.1016/j.tetlet.2017.12.071

  日期：2018.1

  We have investigated synthesis as well as purification of 5,5‴-bis(tridecafluorohexyl)-2,2′:5′,2″:5″,2‴-quaterthiophene (BFH-4 T, n-type organic semiconducting material) using supercritical carbon dioxide (scCO2) as a green solvent. BFH-4T was obtained in good selectivity and high yield by TDAE/PdCl2-catalyzed reductive coupling reaction of 5-bromo-5′-(tridecafluorohexyl)-2,2′-bithiophene in scCO2

  我们研究了5,5′-双（三氟铝己基）-2,2′：5′，2″：5″，2′-四噻吩（BFH-4 T，n型有机半导体材料）的合成及纯化使用超临界二氧化碳（scCO 2）作为绿色溶剂。BFH-4T通过TDAE在良好的选择性和高收率获得/的PdCl 2催化的5-溴-5'的还原偶合反应- （十三氟）-2,2'-二噻吩在SCCO 2。我们还通过将scCO 2传递到反应容器中而成功建立了反应混合物的纯化方法。产物为BFH-4T的黄色粉末，纯度大于99％，并且不包含Pd催化剂。
• Symmetrical and Nonsymmetrical Liquid Crystalline Oligothiophenes: Convenient Synthesis and Transition-Temperature Engineering
  作者：Julie Leroy、Nicolas Boucher、Sergey Sergeyev、Michele Sferrazza、Yves Henri Geerts

  DOI：10.1002/ejoc.200600850

  日期：2007.3

  the aromatic core with two identical branched alkyl chains and (ii) desymmetrization of the molecule with two alkyl substituents of different length or structure. Key steps in the synthesis of symmetrical and nonsymmetrical terthiophenes and quaterthiophenes involve Suzuki coupling and carbanion alkylation. A well-adjusted balance between the π–π stacking of the aromatic core and the disorder caused

  描述了液晶低聚噻吩中转变温度工程的两种方法：(i) 在芳香核处用两个相同的支链烷基取代，以及 (ii) 用两个不同长度或结构的烷基取代基使分子去对称化。对称和非对称三联噻吩和四联噻吩合成的关键步骤涉及 Suzuki 偶联和碳负离子烷基化。芳香核的 π-π 堆积与外围烷基链引起的无序之间的良好平衡被证明对于控制低聚噻吩介晶的热致行为很重要。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• PROCESSES FOR PREPARING CURED FILMS, THE RESULTING FILMS, AND PLASMA-INITIATED POLYMERIZABLE COMPOSITIONS
  申请人：FUJIFILM Corporation

  公开号：US20140170405A1

  公开（公告）日：2014-06-19

  Provided are novel plasma-assisted processes for preparing cured films having excellent heat resistance and moisture resistance. A process for preparing a cured film, comprising at least: applying a composition containing (A) at least one conductive polymer precursor on a substrate to form a coating layer, and irradiating the coating layer with a plasma to polymerize the conductive polymer precursor (A).

  提供了一种新型等离子体辅助制备固化膜的工艺，该固化膜具有优异的耐热性和耐潮性。一种制备固化膜的工艺，包括至少以下步骤：在基板上涂布含有（A）至少一种导电聚合物前体的组合物以形成涂层层，然后用等离子体照射涂层层以聚合导电聚合物前体（A）。
• ORGANIC SEMICONDUCTOR MATERIAL
  申请人：Melucci Manuela

  公开号：US20140217374A1

  公开（公告）日：2014-08-07

  Novel compounds useful as organic semiconductor material are described. Semiconductor devices containing said organic semiconductor material are also described.

  本文描述了一种有用的有机半导体材料的新化合物。同时还描述了含有该有机半导体材料的半导体器件。