1-(hexyl-6'-bromo)-2,5-dimethoxybenzene | 151426-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(hexyl-6'-bromo)-2,5-dimethoxybenzene
• 英文别名: 1-(6-bromohexyl)-2,5-dimethoxybenzene；2-(6-Bromohexyl)-1,4-dimethoxybenzene
• CAS: 151426-30-1
• 化学式: C₁₄H₂₁BrO₂
• 分子量: 301.224
• InChiKey: BMBVWIMMYZQGSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(hexyl-6'-bromo)-2,5-dimethoxybenzene 在 四丁基溴化铵 、 potassium carbonate 、 sodium iodide 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 4-[6-(2,5-dimethoxyphenyl)hexyl-methylamino]benzaldehyde
  参考文献：
  名称：

  Rational designs of multifunctional polymers

  摘要：

  To manifest photorefractive effects, a polymer must possess a photocharge generator, a charge transporter, a charge trapping center, and a nonlinear optical chromophore. We utilized the Stille coupling reaction to synthesize a novel type of multifunctional polymer that contains a conjugated backbone and a second-order NLO chromophore. The expectation that the polymers will possess photorefractivity is the design idea behind the structure of the polymers. Because the conjugated backbone absorbs photons in the visible region and is photoconductive, it is expected to play the triple role of charge generator, charge transporter, and backbone. Thus, the four functionalities necessary to manifest the PR effect will exist simultaneously in a single polymer. The second harmonic generation and the photoconductivity measurements revealed that the polymers are nonlinear-optically active and photoconductive. Two beam-coupling experiments clearly indicated asymmetric optical energy exchange, which is an unambiguous demonstration of photorefractivity.

  DOI：

  10.1021/ja00078a012
• 作为产物：
  描述：

  1,6-二溴己烷 、 对苯二甲醚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以3.8 g的产率得到1-(hexyl-6'-bromo)-2,5-dimethoxybenzene
  参考文献：
  名称：

  Fluorescence Studies of Poly(p-phenyleneethynylene)s: The Effect of Anthracene Substitution

  摘要：

  The poly(p-phenylezthynylene) molecules, PI-PIII, synthesized by a palladium-catalyzed cross-coupling reaction of diiodobenzene derivatives and derivatives of 1,4-diethynylbenzene, are highly luminescent materials. The polymers are soluble by virtue of the -OC16H33 groups introduced on the aromatic rings and by controlling their molecular weight. The fluorescent quantum yields are between 0.35 and 0.40 depending on the material. The excited-state Lifetimes of the polymers are 1-2 ns, slightly shorter than that of the model compound, 1,4-diphenylethynyl-2,5-dibutoxybenzene, which has a lifetime of 3 ns. Incorporation of anthracene, coupled at the 9,10-positions by using 9,10-bibromoanthracene, into the polymer backbone decreases the quantum yield to between 0.05 and 0.27 depending on the anthracene content. In addition, low-energy electronic transitions and longer wavelength emission bands associated with the anthracene group are produced. The polymers harvest optical energy and transfer it to the anthracene resulting in emission from this chromophore. In the case where only terminal anthracene units, introduced by using 9-bromo-10-phenylethynylanthracene, are present, the process is very efficient with >95% of the energy being transferred to the end groups.

  DOI：

  10.1021/j100014a003

文献信息

• Exploration of the Stille Coupling Reaction for the Synthesis of Functional Polymers
  作者：Zhenan Bao、Wai Kin Chan、Luping Yu

  DOI：10.1021/ja00155a007

  日期：1995.12

  The palladium-catalyzed Stille coupling reaction was used for preparing functionalized, conjugated polymers. This reaction has several advantages, two of which are that it requires mild reaction conditions and produces high yields. Several factors which affect the polymerization processes were investigated, such as the catalyst composition and concentration, different solvents and ligands, and structures of monomers. It was found that solvents that could keep the macromolecules in solution and stabilize the palladium(0) catalyst would yield polymers with high molecular weights. If a Pd(II) compound was used as the catalyst, a stoichiometric adjustment of the distannyl monomer was necessary to enhance the molecular weight of the resulting polymer. In general, it was found that a combination of an electron-rich distannyl monomer and an electron-deficient dihalide (ditriflate) monomer forms polymers with relatively high molecular weights. To further demonstrate the versatility of the Stille reaction for polycondensations, different types of conjugated polymers with different properties and applications, such as liquid crystalline conjugated polymers and conjugated photorefractive polymers, were synthesized.