3'-hexyl-2,2':5',2"-terthiophene | 173448-32-3

• 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'-hexyl-2,2':5',2"-terthiophene
• 英文别名: 3'-hexyl-2,2':5',2''-terthiophene；2,2':5',2''-Terthiophene, 3'-hexyl-；3-hexyl-2,5-dithiophen-2-ylthiophene
• CAS: 173448-32-3
• 化学式: C₁₈H₂₀S₃
• 分子量: 332.555
• InChiKey: YTVFFHNAOQSJOY-UHFFFAOYSA-N

物化性质

• 沸点：
  434.5±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  magnesium,2H-thiophen-2-ide,bromide 、 2,5-二溴-3-己基噻吩 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以45%的产率得到3'-hexyl-2,2':5',2"-terthiophene
  参考文献：
  名称：

  Symmetrical alkyl-substituted oligothiophenes as ligands: complexation of the [(η-C5H5)Ru]+ moiety by hexyl-substituted ter-, quater- and quinque-thiophenes

  摘要：

  The soluble, symmetrical oligothiophenes 3,3 "-dihexyl-2,2':5',2 "-terthiophene 7 and 4',3'''-dihexyl-2,2':5',2 ":5",2"':5''', 2""-quinquethiophene 9 and the unsymmetrical oligothiophenes 3'-hexyl-2,2':5',2 "-terthiophene 6 and 3,3 "-dihexyl-2,2':5',2 ":5",2'''-quaterthiophene 11 have been prepared by Kumada-type coupling reactions, using 2-bromothiophene, 2,5-dibromothiophene, 2-bromo-3-hexylthiophene and 2,5-dibromo-3-hexylthiophene as building blocks. Their behaviour as ligands towards the cyclopentadienylruthenium (II) moiety has been examined, by carrying out ligand exchange reactions between [(eta-C5H5)Ru(CH3CN)(3)]PF6 and an excess of the oligothiophene in CH2Cl2, and characterising the product(s) by FAB mass spectrometry and H-1 and C-13{H-1} NMR spectroscopy. Upon complexation of a thiophene ring (eta(5)), the thienyl proton resonances of that ring shift upfield, as do the C-13 resonances. With terthiophene 7, in which the outer thiophene rings bear alkyl groups, the product is [(eta-C5H5)Ru(eta-7)]PF6 13, a single regioisomer in which exclusively an outer thiophene ring is complexed by the cyclopentadienylruthenium (II) moiety. With terthiophene 6, however, in which the inner thiophene ring bears an alkyl substituent, a mixture of all three possible regioisomers of [(eta-C5H5)Ru(eta-6)]PF6 12 is obtained. Similarly, with the symmetrical quinquethiophene 9, two regioisomers of the complex [(eta-C5H5)Ru(eta-9)]PF6 14 are obtained, one in which an outer thiophene ring is complexed, and one in which an inner alkylthiophene ring is complexed. With the unsymmetrical quaterthiophene 11, which includes all four types of thiophene ring (inner and outer alkylthiophene, inner and outer unsubstituted thiophene), 93% of the product [(eta-C5H5)Ru(eta-11)]PF6 15 is the regioisomer in which the outer alkylthiophene ring is complexed. These results show that there are two factors controlling the site of complexation, a tendency for the outermost ring to complex and a tendency for an alkylthiophene ring to complex. Where these conflict, a mixture of regioisomers is obtained. The electrochemistry of both the free oligothiophenes and of their Ru(ll) complexes has been compared. On complexation, there is a substantial positive shift in the oxidation potential of the oligothiophene, and a new, irreversible reduction is observed at ca.-1 V. Although polythiophene films could be deposited by electrooxidation of the free oligothiophenes in acetonitrile, electroactive polymer films could not be deposited by electrooxidation of the complexes in dichloromethane.

  DOI：

  10.1039/a809623f

文献信息

• Synthesis of substituted oligothiophenes and X-ray crystal structures of 3′-methyl-2,2′∶5′,2″-terthiophene, 3,3″-dimethyl-2,2′∶5′,2″-terthiophene and 5′-(2-thienyl)-2,2′∶3′,2″-terthiophene
  作者：Penny A. Chaloner、Sumudu R. Gunatunga、Peter B. Hitchcock

  DOI：10.1039/a607254b

  日期：——

  A range of substituted oligothiophenes has been prepared and characterised. Crystal structures were determined for three substituted terthiophenes. Both in solution and in the solid state, syn-conformers were found to be populated to a greater extent than expected.

  已制备并表征了一系列取代的寡聚噻吩。对三种取代三噻吩的晶体结构进行了测定。在溶液和固态中，发现顺式构象的存在比例超过了预期。
• 3-Fluoro-4-hexylthiophene as a Building Block for Tuning the Electronic Properties of Conjugated Polythiophenes
  作者：Frédéric Gohier、Pierre Frère、Jean Roncali

  DOI：10.1021/jo302571u

  日期：2013.2.15

  3-Fluoro-4-hexylthiophene has been prepared by a synthetic route involving perbromination of 3-hexylthiophene followed by protection of the 2- and 5-positions of thiophene by trimethylsilyl groups and bromine/fluorine exchange. As expected, 3-hexyl-4-fluorothiophene oxidizes at a higher potential than 3-hexylthiophene; however, all attempts to electropolymerize this new thiophenic monomer have remained unsuccessful. Three terthienyls containing 3-hexylthiophene, 3-fluoro-4-hexylthiophene, and 3-bromo-4-hexylthiophene as the median group have been synthesized and used as substrates for electropolymerization. The electronic properties of the starting terthienyls and the resulting polymers have been analyzed by cyclic voltammetry and UV-vis spectroscopy, and the effects of substitution of the median thiophene ring are discussed.
• ORGANIC PHOTOELECTRIC CONVERSION ELEMENT
  申请人：Uetani Yasunori

  公开号：US20120100285A1

  公开（公告）日：2012-04-26

  An organic photoelectric conversion element having a high absorbance at 600 nm can be provide by a method for manufacturing an organic photoelectric conversion element having a pair of electrodes at least one of which is transparent or translucent, and an organic layer between the electrodes, the method comprising a step of applying a solution that contains a conjugated polymer compound having a thiophenediyl group as a repeating unit and a sulfur-containing heterocyclic compound on one of the electrodes to form an applied film, and a step of drying the applied film at a temperature of 70° C. or less to form the organic layer.
• US8723163B2
  申请人：——

  公开号：US8723163B2

  公开（公告）日：2014-05-13