tributyl(5,5''-dihexyl-[2,2';3',2'']terthiophen-5'-yl)stannane | 442911-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: tributyl(5,5''-dihexyl-[2,2';3',2'']terthiophen-5'-yl)stannane
• CAS: 442911-12-8
• 化学式: C₃₆H₅₈S₃Sn
• 分子量: 705.765
• InChiKey: BBGAHWXNCCONEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.64
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tributyl(5,5''-dihexyl-[2,2';3',2'']terthiophen-5'-yl)stannane 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 tributyl-{2,3-di(5,5''-dihexyl-[2,2';3',2'']terthiophen-5'-yl)thiophen-5-yl}stannane
  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) 、 正丁基锂 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 tributyl(5,5''-dihexyl-[2,2';3',2'']terthiophen-5'-yl)stannane
  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

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。
• The synthesis and properties of solution processable phenyl cored thiophene dendrimers
  作者：William J. Mitchell、Nikos Kopidakis、Garry Rumbles、David S. Ginley、Sean E. Shaheen

  DOI：10.1039/b508683c

  日期：——

  In this paper we describe the convergent synthesis of a new class of phenyl cored thiophene dendrimers, which are promising candidates for use in organic semiconductor devices. We have prepared dendrimers with three and four dendrons around the core as well as dendrimers with 1st and 2nd generation dendrons. All the dendrimers were soluble in common organic solvents such as chloroform, THF and toluene. The structures and size properties are confirmed by a number of techniques including NMR, GPC and MALDI-TOF-MS. Decomposition was studied by TGA with initial breakdown of the hexyl surface groups followed by the aromatic core. The spectroscopic properties were studied by UV-vis and PL spectrometry which demonstrated substantial differences between the dendrimers with three and four dendrons. Optical band gaps varied between 2.34 and 2.60 eV for thin films of the dendrimers and electronic band gaps were, on average, 0.3 eV greater than the optical band gaps. The smallest band gap was measured for the dendrimer with four 2nd generation dendrons around the phenyl core. Fluorescence lifetimes of the molecules in solution ranged from 200 to 560 ps. This range in values was attributed to differences in internal conversion rates associated with varying degrees of flexibility of the extended dendrons.

  在本文中，我们介绍了一种新型苯基芯噻吩树枝形分子的聚合合成方法，这种树枝形分子有望用于有机半导体器件。我们制备了核心周围有三个和四个树枝状分子的树枝状聚合物，以及有第一代和第二代树枝状分子的树枝状聚合物。所有树枝状聚合物均可溶于氯仿、四氢呋喃和甲苯等常见有机溶剂。核磁共振、气相色谱和 MALDI-TOF-MS 等多种技术证实了它们的结构和尺寸特性。通过热重分析法研究了分解情况，首先分解的是己基表面基团，然后是芳香族核心。通过紫外-可见光光谱法和聚光光谱法对光谱特性进行了研究，结果表明具有三个和四个树枝的树枝状聚合物之间存在很大差异。树枝状聚合物薄膜的光学带隙介于 2.34 和 2.60 eV 之间，电子带隙平均比光学带隙大 0.3 eV。苯核周围有四个第二代树枝状分子的树枝状聚合物的带隙最小。溶液中分子的荧光寿命从 200 到 560 ps 不等。之所以会出现这样的数值范围，是因为扩展树枝的柔韧性不同，内部转换率也不同。
• 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.
• Highly Sensitive and Selective “Turn-on” Calcium Cation Sensing from a Dendronic Terthiophene Tetraethylene Glycol (TEG) Molecule
  作者：Yushin Park、Dahlia C. Apodaca、Jonathan Pullen、Rigoberto C. Advincula

  DOI：10.1021/jp1068522

  日期：2010.10.21

  A molecule consisting of a branched or dendronic terthiophene with tetraethylene glycol moiety (3T5O) was synthesized for highly sensitive and selective calcium ion detection in solution. The sulfur atoms of the terthiophene dendron moiety contribute to the metal-ligand complexation of calcium cations. The modification of the terthiophene dendrons with a hydroxyl-terminated tetracthylene glycol (TEG) group produces a twisted intramolecular charge transfer (TICT) event in which the terthiophene moiety is conformationally twisted, affecting its chromophoric and fluorophoric activity. This twisted conformation resulted in an increase Ill emission intensity at 320 nm, at the same time producing a blue shift in the absorption spectra. This process enabled a "turn-on" system for calcium ion detection compared to most "turn-off" systems involving a quenching route. The intensity of the emission is related to saturation of the terthiophene moiety at a concentration of 3T5O:[Ca2+] 1:4, of similar to 1 x 10(-8) M, which indicates high sensitivity for calcium cations. No response with other cations such as Nal(+), K+, and Mg2+ was observed, which also indicates high selectivity for the system. Conformational analysis of the 3T5O and the twisted terthiophene dendron geometry was done by semiempirical PM3 modeling. In an effort to distinguish specific interactions between monovalent and divalent cations and the 3T5O, restricted Hartree-Fock level calculations using the STO-3G basis set were also performed. The calculations correlated with the experimental results.
• Multi-thiophene-substituted NIR boron-dibenzopyrromethene dyes: synthesis and their spectral properties
  作者：Yukie Suda、Ryuhei Nishiyabu、Yuji Kubo

  DOI：10.1016/j.tet.2015.04.094

  日期：2015.6

  Thiophene-substituted boron-dibenzopyrromethene dyes has been synthesized and characterized. We found that the optical properties of dithienyl-substituted dibenzo-BODIPYs depend on the substituted pattern. Namely, thiophene substitutions at the 5,5'-positions of the isoindole rings (5-2T) led to a bathochromic shift of 37 nm and an increase in the molar extinction coefficient (epsilon), whereas the replacement of the phenyl rings with thiophene rings at the 3,3'-positions (3-2T) resulted in a significant decrease of the e value, despite a large bathochromic shift of 65 nm. The emission properties were also characterized; the replacement of phenyl units with thiophene units at the 3,3'-positions led to a larger Stokes shift than that of thiphene-free dibenzo-BODIPY 0T, which was rationalized to occur through geometry relaxation upon photoexcitation. Newly synthesized dendritic oligothiophene dibenzo-BODIPY conjugates have emitted near-infrared light at 766 nm when excited with UV light, through fluorescence resonance energy transfer (FRET) from the thiophene dendron unit to the dibenzo-BODIPY core. (C) 2015 Elsevier Ltd. All rights reserved.