5-octyl-2,2':5',2"-terthiophene | 172514-65-7

• 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
• 英文名称: 5-octyl-2,2':5',2"-terthiophene
• 英文别名: 5-octyl-(2,2',5',2''-terthiophene)；5-octyl-2,2',5',2''-terthiophene；2-Octyl-5-(5-thiophen-2-ylthiophen-2-yl)thiophene
• CAS: 172514-65-7
• 化学式: C₂₀H₂₄S₃
• 分子量: 360.609
• InChiKey: ZWDXICIQFOAVBL-UHFFFAOYSA-N

物化性质

• 沸点：
  454.2±40.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-octyl-2,2':5',2"-terthiophene 在 正丁基锂 、 ammonium acetate 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 2-(5-octyl-(2,2',5',2''-terthiophen)-5''-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Toward Optimization of Oligothiophene Antennas: New Ruthenium Sensitizers with Excellent Performance for Dye-Sensitized Solar Cells

  摘要：

  This paper reports on the design and synthesis of three new ruthenium sensitizers, as well as the optimization of their linear or dendritic light-harvesting oligothiophene antennas to achieve superior device performance. The three new ruthenium sensitizers, [Ru(dcbpy)(obtip)(NCS)(2)] (JF-5, dcbpy = 4,4'-dicarboxylic obtip = 2-(5-octyl-(2,2'-bithiophen)-5'-yl)-1H-imidazo[4,51][1,10]-phenanthroline), [Ru(dcbpy)(ottip)(NCS)(2)] (JF-6, ottip = 2-(5-octyl-2,2',5',2 ''-terthiophen)-5 ''-yl)-1H-imidazo[4,5-f][1,10]-phenanthroline), and [Ru(dcbpy)(dottip)(NCS)(2)] (JF-7, dottip = di-(5-octylthiophen-2-ypthiophen-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline), were synthesized in a typical one-pot reaction. The ruthenium sensitizer JF-5 incorporating a linear and planar 2,2'-bithiophene antenna showed the best DSCs performance (9.5%; compared to N3, 8.8%). The difference in the performance of these sensitizers demonstrates that elongating the linear and planar light-harvesting antenna result in an enhancement in MLCT intensity, but a reduction in the quantity of dye-loading. This finding not only permitted the power-conversion efficiency in ruthenium sensitizers containing oligothiophene antennas to be optimized, but also points to a promising direction for molecule engineering in DSCs.

  DOI：

  10.1021/cm100770x
• 作为产物：
  描述：

  5-正辛基-2,2'-并噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 24.25h， 生成 5-octyl-2,2':5',2"-terthiophene
  参考文献：
  名称：

  Photorefractive effect of photoconductive ferroelectric liquid crystalline mixtures composed of photoconductive chiral compounds and liquid crystal

  摘要：

  这项研究调查了含有光导性手性化合物的光导性铁电液晶(FLCs)的光折变效应。研究人员合成了一系列新型光导性手性化合物。选择了具有四种手性结构的三联噻吩化合物作为光导性手性化合物，并将其与非手性向列相C液晶混合。这些混合物呈现铁电手性向列相C相。通过双光束耦合实验研究了混合物的光折变性。研究发现，含有光导性手性化合物的FLCs表现出110 cm⁻¹的大增益系数和5毫秒的快速响应时间。

  DOI：

  10.1039/c1jm10405e

文献信息

• PHOTOSENSITIZER DYE
  申请人：Wu Chun-Guey

  公开号：US20070265443A1

  公开（公告）日：2007-11-15

  A photosensitizer dye is provided. The photosensitizer dye contains a Ru complex represented by the following formula (1): wherein Y 1 and Y 2 independently represents hydrogen atom (H), lithium (Li), sodium (Na) or tetra-alkyl ammonium groups (as represented by the following general formula (2)). Formula (2): wherein A, B, C and D independently represents C m H 2m+1 (m=1˜6). Wherein X 1 represents one of the following formulas (3)˜(8) and X 2 represents H or a group the same as X 1 ,

  提供了一种光敏染料。该光敏染料包含由以下公式（1）表示的Ru配合物：其中Y1和Y2分别表示氢原子（H）、锂（Li）、钠（Na）或四烷基铵基团（如以下一般公式（2）所表示）。公式（2）：其中A、B、C和D分别表示CmH2m+1（m=1～6）。其中X1表示以下公式（3）～（8）中的一种，X2表示H或与X1相同的基团。
• 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)
• 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：——
• US7321037B2
  申请人：——

  公开号：US7321037B2

  公开（公告）日：2008-01-22
• Toward Optimization of Oligothiophene Antennas: New Ruthenium Sensitizers with Excellent Performance for Dye-Sensitized Solar Cells
  作者：Jen-Fu Yin、Jian-Ging Chen、Zong-Zhan Lu、Kuo-Chuan Ho、Hong-Cheu Lin、Kuang-Lieh Lu

  DOI：10.1021/cm100770x

  日期：2010.8.10

  This paper reports on the design and synthesis of three new ruthenium sensitizers, as well as the optimization of their linear or dendritic light-harvesting oligothiophene antennas to achieve superior device performance. The three new ruthenium sensitizers, [Ru(dcbpy)(obtip)(NCS)(2)] (JF-5, dcbpy = 4,4'-dicarboxylic obtip = 2-(5-octyl-(2,2'-bithiophen)-5'-yl)-1H-imidazo[4,51][1,10]-phenanthroline), [Ru(dcbpy)(ottip)(NCS)(2)] (JF-6, ottip = 2-(5-octyl-2,2',5',2 ''-terthiophen)-5 ''-yl)-1H-imidazo[4,5-f][1,10]-phenanthroline), and [Ru(dcbpy)(dottip)(NCS)(2)] (JF-7, dottip = di-(5-octylthiophen-2-ypthiophen-5-yl)-1H-imidazo[4,5-f][1,10]phenanthroline), were synthesized in a typical one-pot reaction. The ruthenium sensitizer JF-5 incorporating a linear and planar 2,2'-bithiophene antenna showed the best DSCs performance (9.5%; compared to N3, 8.8%). The difference in the performance of these sensitizers demonstrates that elongating the linear and planar light-harvesting antenna result in an enhancement in MLCT intensity, but a reduction in the quantity of dye-loading. This finding not only permitted the power-conversion efficiency in ruthenium sensitizers containing oligothiophene antennas to be optimized, but also points to a promising direction for molecule engineering in DSCs.