{4-[(E)-3,4-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-hex-3-ene-1,5-diynyl]-phenyl}-dimethyl-amine | 326500-36-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: {4-[(E)-3,4-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-hex-3-ene-1,5-diynyl]-phenyl}-dimethyl-amine
• 英文别名: 4-[(E)-3,4-bis[[tert-butyl(dimethyl)silyl]oxymethyl]hex-3-en-1,5-diynyl]-N,N-dimethylaniline
• CAS: 326500-36-1
• 化学式: C₂₈H₄₅NO₂Si₂
• 分子量: 483.842
• InChiKey: QBTHYCIGMXCVQC-OCOZRVBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {4-[(E)-3,4-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-hex-3-ene-1,5-diynyl]-phenyl}-dimethyl-amine 在 四甲基乙二胺 、 氧气 、 copper(l) chloride 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 2.0h， 以63%的产率得到(E,E)-3,4,9,10-Tetrakis{[(tert-butyl)dimethylsilyloxy]methyl}-1,12-bis[4-(dimethylamino)phenyl]dodeca-3,9-diene-1,5,7,11-tetrayne
  参考文献：
  名称：

  供体/受体取代的四乙炔：用于先进材料的分子的系统组装

  摘要：

  制备了带有电子给体（对甲氧基苯基或对氨基苯基）和/或电子接受性（对硝基苯基）基团的一系列全面的四乙炔基（= 3,4-二乙炔基己烯-3-烯-1,5-二炔，TEE）通过[Pd]催化的Sonogashira交叉偶联反应。研究了这些分子的电子和光子特性，并特别强调了由中心TEE核心周围的供体/受体取代程度和模式所引起的影响。该分析表明，分子内供体-受体相互作用（如长波长电荷转移带所证明）在TEE 44和46中显着更有效，反式和顺，线性缀合供体和受体之间的电子通路，比11，与孪位的，交叉共轭的电子通道。UV / VIS光谱揭示的最长波长吸收带（λ的稳定红移最大）作为供体-受体共轭路径的数目在从双-芳基化的变化增加（11，44，和46），以四-芳基化（14 ，31和35）TEE。还发现最长波长吸收的位置强烈依赖于R 2 NC 6 H 4中N-取代基的性质。-捐助团体。电子发射光谱研究表明，供体-受体取

  DOI：

  10.1002/hlca.19960790818
• 作为产物：
  描述：

  [(E)-3,4-bis[[tert-butyl(dimethyl)silyl]oxymethyl]hex-3-en-1,5-diynyl]-trimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 26.0h， 生成 {4-[(E)-3,4-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-hex-3-ene-1,5-diynyl]-phenyl}-dimethyl-amine
  参考文献：
  名称：

  供体/受体取代的四乙炔：用于先进材料的分子的系统组装

  摘要：

  制备了带有电子给体（对甲氧基苯基或对氨基苯基）和/或电子接受性（对硝基苯基）基团的一系列全面的四乙炔基（= 3,4-二乙炔基己烯-3-烯-1,5-二炔，TEE）通过[Pd]催化的Sonogashira交叉偶联反应。研究了这些分子的电子和光子特性，并特别强调了由中心TEE核心周围的供体/受体取代程度和模式所引起的影响。该分析表明，分子内供体-受体相互作用（如长波长电荷转移带所证明）在TEE 44和46中显着更有效，反式和顺，线性缀合供体和受体之间的电子通路，比11，与孪位的，交叉共轭的电子通道。UV / VIS光谱揭示的最长波长吸收带（λ的稳定红移最大）作为供体-受体共轭路径的数目在从双-芳基化的变化增加（11，44，和46），以四-芳基化（14 ，31和35）TEE。还发现最长波长吸收的位置强烈依赖于R 2 NC 6 H 4中N-取代基的性质。-捐助团体。电子发射光谱研究表明，供体-受体取

  DOI：

  10.1002/hlca.19960790818

文献信息

• Donor/Acceptor-Substituted Tetraethynylethenes: Systematic Assembly of Molecules for Use as Advanced Materials
  作者：Rik R. Tykwinski、Martin Schreiber、Raquel Pérez Carlón、François Diederich、Volker Gramlich

  DOI：10.1002/hlca.19960790818

  日期：1996.12.11

  such as 11 or 44, in agreement with the presence of highly polarized excited states in these molecules. Correspondingly, fluorescence spectra of TEEs bearing only donor or acceptor substituents showed little solvent dependency. The large majority of the donor/acceptor-substituted TEEs are thermally and environmentally stable molecules. They can be stored for months as solids in the air at room temperature

  制备了带有电子给体（对甲氧基苯基或对氨基苯基）和/或电子接受性（对硝基苯基）基团的一系列全面的四乙炔基（= 3,4-二乙炔基己烯-3-烯-1,5-二炔，TEE）通过[Pd]催化的Sonogashira交叉偶联反应。研究了这些分子的电子和光子特性，并特别强调了由中心TEE核心周围的供体/受体取代程度和模式所引起的影响。该分析表明，分子内供体-受体相互作用（如长波长电荷转移带所证明）在TEE 44和46中显着更有效，反式和顺，线性缀合供体和受体之间的电子通路，比11，与孪位的，交叉共轭的电子通道。UV / VIS光谱揭示的最长波长吸收带（λ的稳定红移最大）作为供体-受体共轭路径的数目在从双-芳基化的变化增加（11，44，和46），以四-芳基化（14 ，31和35）TEE。还发现最长波长吸收的位置强烈依赖于R 2 NC 6 H 4中N-取代基的性质。-捐助团体。电子发射光谱研究表明，供体-受体取
• Synthesis and Physical Investigation of Donor–Donor and Acceptor–Acceptor End-Functionalized Monodisperse Poly(triacetylene) Oligomers
  作者：Rainer E. Martin、Ulrich Gubler、Corinne Boudon、Christian Bosshard、Jean-Paul Gisselbrecht、Peter Günter、Maurice Gross、François Diederich

  DOI：10.1002/1521-3765(20001201)6:23<4400::aid-chem4400>3.0.co;2-a

  日期：2000.12.1

  Two series of monodisperse, terminally donor-donor [D-D, D=4-(dimethylamino)phenyl] and acceptor-acceptor [A-A, A=4-nitrophenyl] functionalized poly(triacetylene) (PTA) oligomers ranging from monomer to hexamer were synthesized by oxidative Hay oligomerization under end-capping conditions. The corresponding D-D and A-A end-substituted polymers with an average degree of polymerization (DP) of n approximate to 18 and n approximate to 12, respectively, were also prepared and served as reference points for the corresponding infinitely long polymers. These terminally functionalized PTA oligomers and polymers are yellow- to orange-colored compounds, displaying excellent solubility in aprotic solvents with melting points above 200 degreesC for the hexamers. For the 4-(dimethylamino)phenyl substituted compounds, a consistent first oxidation potential around + 0.42 V versus Fc/Fc(+) (ferrocene/ferricinium) was observed, whereas the 4-nitrophenyl functionalized systems underwent a reversible reductive two-electron transfer around -1.40 V versus Fc/Fc(+). The nature of the end-groups has a dramatic influence on the electronic absorption spectra. Saturation of the linear optical properties in the D-D series occurs at significantly shorter chain-length [effective conjugation length (ECL) of n approximate to 4 monomer units] than in the A-A substituted or the previously reported Me3Si- and Et3Si-end-capped PTA oligomer series (ECL: n approximate to 10 monomer units). Similar observations with respect to the ECL were made by measurement of the Raman-active <()over tilde>((C=C)) stretches. Third-harmonic generation (THG) and degenerate four-wave mixing (DFWM) experiments showed that shorter oligomers of terminally D-D or A-A functionalized PTAs display higher second hyperpolarizabilities gamma than the corresponding R3Si-end-capped series (R=alkyl), Moreover, they disclose a distinct peak of the nonlinearity per monomer unit at intermediate backbone lengths. In THG experiments, the second hyperpolarizabilities for long D/A-functionalized PTA oligomers attained the same saturation values as observed for the corresponding R3Si-end-capped rods. The nonlinearities measured by DFWM of the D-D and A-A substituted PTAs were found to be larger than for the silylated ones, which can be explained by the closeness of the two-photon resonance.