5,5''-dihexyl-[2,2';3',2'']terthiophene | 442911-11-7

• 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: 5,5''-dihexyl-[2,2';3',2'']terthiophene
• 英文别名: 5,5''-dihexyl-2,2':3',2''-terthiophene；2,3-bis(5-hexylthiophen-2-yl)thiophene
• CAS: 442911-11-7
• 化学式: C₂₄H₃₂S₃
• 分子量: 416.716
• InChiKey: ZNIYSRUMVSCGOR-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

反应信息

• 作为反应物：
  描述：

  5,5''-dihexyl-[2,2';3',2'']terthiophene 在 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 2,3-di(5,5''-dihexyl-[2,2';3',2'']terthiophen-5'-yl)thiophene
  参考文献：
  名称：

  Synthesis and enhanced electron transfer of supramolecular nano-composite containing dendritic dye and surface-modified ZnO nano-rods

  摘要：

  Supramolecular nano-composites 15T5N/ZnOx-PNH containing enhanced compatibilities of dendritic dye 15T5N and surface-modified nano-rod ZnOx-PNH were developed in this study. The physical properties of supramolecular nano-composites have been well investigated by theoretical calculation and various measurements, including UV visible, PL, TEM, TCSPC, FT-IR, and CV. H-bonded nano-composite 15T5N/ZnO30-PNH possessed the saturated quenched fiuorscence as dendritic dye 15T5N complexed with surface-modified nano-rod ZnO30-PNH. In contrast to nano-rod mixture 15T5N/ZnO (without surface-modification), more widened visible absorption band to promote more efficient photo-induced charge separation phenomenon was observed in supramolecular nano-composite 15T5N/ZnO30-PNH. Compared with surfactant T-PNH, less efficient electron transfer of surfactant T-PC6 was observed in TCSPC and PL measurements because of the steric hindrance of long alkyl chains (-C6H13) attached to surfactant T-PC6. Therefore, the triple H-bonds between dendritic dye 15T5N and surface-modified nano-rod ZnO30-PNH are verified to result in the desirable effective electron transfer in supramolecular nano-composite 15T5N/ZnO30-PNH.

  DOI：

  10.1016/j.dyepig.2018.04.052
• 作为产物：
  描述：

  2-正己基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 碘 、 magnesium 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 24.0h， 生成 5,5''-dihexyl-[2,2';3',2'']terthiophene
  参考文献：
  名称：

  Synthesis and photovoltaic properties of a star-shaped molecule based on a triphenylamine core and branched terthiophene end groups

  摘要：

  我们合成了一种新的星形供体-受体分子，可用作溶液处理大块异质结有机太阳能电池（OSC）的供体材料。该分子由一个作为核心的三苯胺（TPA）单元和一个具有三个臂的供体单元组成，三个臂分别含有苯并[1,2,5]噻二唑（BT）受体单元和 5,5″-二己基-2,2′:3′,2″-噻吩（tTh）末端基团。该分子被命名为 S(TPA-BT-tTh)，在波长 300-650 纳米范围内具有宽吸收带，空穴迁移率高达 1.1×10-4 cm2 V-1 s-1。以 S（TPA-BT-tTh）为供体、[6,6]-苯基 C71-丁酸甲酯（PC70BM）为受体（1:3，w/w）的 OSC 器件在 AM.1.5 和 100 mW/cm2 的照明条件下，功率转换效率为 2.28%，短路电流密度为 6.39 mA/cm2。

  DOI：

  10.1007/s11426-013-4878-9

文献信息

• Hybrid organic–inorganic nanomaterials based on polythiophene dendronized nanoparticles
  作者：Rigoberto C. Advincula

  DOI：10.1039/b517601h

  日期：——

  dendron and nature of binding on semiconductor nanocrystals. In the other system using the direct capping method, the size of the Au nanoparticle is mediated by the dimensions of the ligand, i.e. alkyl chain spacer and dendron branching or size. These hybrid dendron/nanoparticle complexes are generally very soluble and stable in non-polar solvents. They exhibit energy transfer, surface plasmon resonance

  在这项工作中，描述了支化寡金属噻吩树枝状分子的合成，表征和应用，所述树枝状寡噻吩树枝状分子用作封端金金属纳米粒子和CdSe量子点的电活性表面活性剂。两种不同的方法已用于合成：配体交换过程和直接封端合成方法。使用紫外可见吸收，FT-IR，AFM，TEM和光致发光光谱学详细研究了每个纳米晶体的树枝状分子的覆盖范围，表面配位相互作用的性质以及能量转移相互作用。树枝状分子的大小和在半导体纳米晶体上结合的性质突出了配位体置换中的竞争/位移。在另一个使用直接封盖方法的系统中，金纳米颗粒的大小由配体的大小来调节，即 烷基链间隔基和树枝状分支或大小。这些杂化树突/纳米粒子复合物通常在非极性溶剂中非常易溶且稳定。它们在金属/半导体与共轭配体之间表现出能量转移，表面等离振子共振效应以及光诱导的电荷转移相互作用。观察到在云母和石墨表面上的吸附。制作了一层光伏电池以证明其在设备应用中的潜力。
• Hybrid Gold-Nanoparticle-Cored Conjugated Thiophene Dendrimers: Synthesis, Characterization, and Energy-Transfer Studies
  作者：Suxiang Deng、Timothy M. Fulghum、Greg Krueger、Derek Patton、Jin-Young Park、Rigoberto C. Advincula

  DOI：10.1002/chem.201100246

  日期：2011.8.1

  A series of hybrid Au‐nanoparticle‐dendrimer materials: nanoparticle‐cored thiophene dendrimers (NCTDs) were synthesized, characterized, and investigated for their energy‐transfer properties. These hybrid nanoparticles were obtained by the simultaneous and in situ reduction of gold(III) chloride and self‐assembly of the thiol‐containing thiophene dendritic ligands. The dendron ligands were radially

  合成，表征和研究了一系列杂化的金纳米粒子树状聚合物材料：纳米粒子核心的噻吩树状聚合物（NCTD）。这些杂化的纳米颗粒是通过同时还原氯化金（III）和含硫醇的噻吩树枝状配体的自组装而获得的。将树枝状配体径向附着在金纳米颗粒上，并通过TEM，UV / Vis，1分析1 H NMR和FTIR光谱。附着的噻吩树突的溶液荧光逐渐淬灭。烷基链长度和树突尺寸均对能量转移效率以及金纳米颗粒的核尺寸和尺寸分布有重要影响。尽管该现象依赖于纳米颗粒尺寸，但是能量转移通常遵循1 / d 2距离依赖关系。单个NCTD纳米颗粒也被吸附在高度有序的热解石墨（HOPG）上，并且在云母平板基底上观察到均匀的聚集体。
• A First Synthesis of Thiophene Dendrimers
  作者：Chuanjun Xia、Xiaowu Fan、Jason Locklin、Rigoberto C. Advincula

  DOI：10.1021/ol025943a

  日期：2002.6.1

  [GRAPHIC]Thiophene dendrons and dendrimers were designed and synthesized using a convergent approach. Metal-mediated coupling reactions were used in the synthesis. A rational approach allowed the formation of alphaalpha, betabeta, and alphabeta linkages between the dendrons and thiophene units.
• Thiophene Dendron Jacketed Poly(amidoamine) Dendrimers:  Nanoparticle Synthesis and Adsorption on Graphite
  作者：Suxiang Deng、Jason Locklin、Derek Patton、Akira Baba、Rigoberto C. Advincula

  DOI：10.1021/ja046144l

  日期：2005.2.1

  The peripheral functionalization of amine-terminated fourth-gene ration poly(amidoamine) (PAMAM) with thiophene dendrons and the preparation of dendrimer-encapsulated metal nanoparticles are described. Interesting nanoparticle stabilization and energy-transfer properties were observed with these hybrid materials. The synthesis involved imine coupling of the dendron derivatives to the peripheral amine groups of PAMAM followed by reduction. The formation of these metal-organic nanoparticle hybrid materials was monitored by UV-vis spectroscopy. The complexation of metal ions and the stabilization effect of PAMAM on metal nanoparticles were investigated by FT-IR. Energy transfer was observed between the metal surface plasmon absorption and fluorescence of the terthiophene dendrons. Non-contact magnetic-AC mode AFM imaging revealed the formation of monodispersed and very stable nanoparticles adsorbed on an HOPG flat substrate.