5-hexanoyl-2,2':5',2''-terthiophene | 173198-21-5

• 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: 5-hexanoyl-2,2':5',2''-terthiophene
• 英文别名: 5-hexanoyl-2,2':5',2"-terthiophene；2-(2-Thienyl)-5-[5-(1-oxohexyl)-2-thienyl]thiophene；1-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]hexan-1-one
• CAS: 173198-21-5
• 化学式: C₁₈H₁₈OS₃
• 分子量: 346.538
• InChiKey: CPZOFTMOBKHNAU-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  494.6±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hexanoyl-2,2':5',2''-terthiophene 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 以71%的产率得到5-hexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Syntheses and Properties of Oligothiophenes with Cyano and Hexyl Groups

  摘要：

  介绍了在四分之一噻吩和三噻吩末端带有氰基和己基的新型低聚噻吩的合成过程。DSC 和偏振显微镜的观察结果表明，在很宽的温度范围内都存在液晶（LC）相。根据吸收和光致发光（PL）光谱以及循环伏安法讨论了能隙问题。通过原子力显微镜 (AFM) 和 X 射线衍射 (XRD) 测量研究了通过真空沉积制造的低聚噻吩薄膜。

  DOI：

  10.1246/cl.2006.280
• 作为产物：
  描述：

  alpha-三联噻吩 、 己酰氯 在 zinc(II) chloride 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以27%的产率得到5-hexanoyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Syntheses and Properties of Oligothiophenes with Cyano and Hexyl Groups

  摘要：

  介绍了在四分之一噻吩和三噻吩末端带有氰基和己基的新型低聚噻吩的合成过程。DSC 和偏振显微镜的观察结果表明，在很宽的温度范围内都存在液晶（LC）相。根据吸收和光致发光（PL）光谱以及循环伏安法讨论了能隙问题。通过原子力显微镜 (AFM) 和 X 射线衍射 (XRD) 测量研究了通过真空沉积制造的低聚噻吩薄膜。

  DOI：

  10.1246/cl.2006.280

文献信息

• Three-dimensional tetra(oligothienyl)silanes as donor material for organic solar cells
  作者：Sophie Roquet、R?mi de Bettignies、Philippe Leriche、Antonio Cravino、Jean Roncali

  DOI：10.1039/b604261a

  日期：——

  Tetrahedral conjugated systems involving four conjugated oligothiophene chains fixed onto a central silicon node (1, 2) have been synthesized and used as donor materials in hetero-junction solar cells. Bilayer solar cells have been realized by thermal evaporation of compounds 1 and 2 as donors and N,N′-bis-tridecylperylenedicarboxyimide as an acceptor. Comparison of the performances of these devices to those of a reference system based on dihexylterthienyl (H3T) shows that despite comparable effective conjugation lengths, the 3D compounds 1 and 2 lead to a power conversion efficiency four–five times higher, suggesting better absorption of the incident light and better hole transport properties. Whereas fabrication of bulk hetero-junction with H3T was prevented by the lack of film forming properties, a prototype bulk hetero-junction based on compound 2 as the donor and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as the acceptor has been realized. A short-circuit current density of 1.13 mA cm−2 and a power conversion efficiency of 0.30% has been measured under AM 1.5 simulated solar irradiation at 80 mW cm−2.

  四面体共轭体系包括固定在中央硅节点上的四条共轭低聚噻吩链（1、2），已被合成并用作异质结太阳能电池的供体材料。以化合物 1 和 2 作为给体，以 N,N′-双十三烷基过二羧酰亚胺作为受体，通过热蒸发实现了双层太阳能电池。将这些器件的性能与基于二己基三噻吩（H3T）的参考系统的性能进行比较后发现，尽管有效共轭长度相当，但三维化合物 1 和 2 的功率转换效率要高出四至五倍，这表明它们对入射光的吸收更好，空穴传输性能也更好。由于 H3T 缺乏成膜特性，因此无法制作体异质结，而以化合物 2 为供体、[6,6]-苯基-C61-丁酸甲酯（PCBM）为受体的体异质结原型已经实现。在 80 mW cm-2 的 AM 1.5 模拟太阳辐照条件下，测得短路电流密度为 1.13 mA cm-2，功率转换效率为 0.30%。
• Syntheses and Properties of Oligothiophenes with Cyano and Hexyl Groups
  作者：Hiroshi Wada、Tomohiro Taguchi、Masanao Goto、Takuya Kambayashi、Takehiko Mori、Ken Ishikawa、Hideo Takezoe

  DOI：10.1246/cl.2006.280

  日期：2006.3

  Syntheses of new oligothiophenes which have cyano and hexyl groups at the ends of quarter- and ter-thiophenes are described. The observations of DSC and polarizing microscopy indicate the presence of liquid-crystalline (LC) phases over a wide temperature range. The energy gaps are discussed on the basis of the absorption and photoluminescence (PL) spectra and cyclic voltammetry. Thin films of oligothiophenes fabricated by vacuum deposition are investigated by AFM and XRD measurements.

  介绍了在四分之一噻吩和三噻吩末端带有氰基和己基的新型低聚噻吩的合成过程。DSC 和偏振显微镜的观察结果表明，在很宽的温度范围内都存在液晶（LC）相。根据吸收和光致发光（PL）光谱以及循环伏安法讨论了能隙问题。通过原子力显微镜 (AFM) 和 X 射线衍射 (XRD) 测量研究了通过真空沉积制造的低聚噻吩薄膜。
• 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
  作者：Byron, David、Matharu, Avtar、Wilson, Robert、Wright, Gavin

  DOI：——

  日期：——
• One-dimensional porphyrin H-aggregates induced by solvent polarity
  作者：Myung-Seok Choi

  DOI：10.1016/j.tetlet.2008.09.140

  日期：2008.12

  A series of new porphyrin derivatives possessing the side arms of alkyl-substituted thiophene oligomer were synthesized. The effects of solvent polarity on the formation of supramolecular assembly have been studied by UV-vis absorption, fluorescence emission, and TEM measurement. The linear-shape porphyrin derivatives bearing two thiophene pentamers at meso-position showed the significant spectral changes in both blue-shift and band broadening of Soret bands which indicate the formation of a relatively larger porphyrin H-aggregate that occurred in nonpolar solvent such as n-hexane. (c) 2008 Elsevier Ltd. All rights reserved.