1-n-hexadecyl-4-[4-N,N-(dimethylamino)styryl]pyridinium bromide | 124730-59-2

• 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-n-hexadecyl-4-[4-N,N-(dimethylamino)styryl]pyridinium bromide
• 英文别名: (E)-N-hexadecyl-4-(2-(4-(dimethylamino)phenyl)ethylene)pyridinium bromide；trans-(E)-N-hexadecyl-4-(N',N'-dimethylamino)stilbazoliumbromide；(E)-N-n-hexadecyl-4-(2-(4-(dimethylamino)phenyl)ethenyl)pyridinium bromide；(E)-N-hexadecyl-N',N'-dimethylamino-stilbazolium bromide；(e)-N-hexadecyl-4-(2-(4-dimethylaminophenyl)ethenyl) pyridinium bromide；4-[(E)-2-(1-hexadecylpyridin-1-ium-4-yl)ethenyl]-N,N-dimethylaniline;bromide
• CAS: 124730-59-2
• 化学式: Br*C₃₁H₄₉N₂
• 分子量: 529.647
• InChiKey: VDUFFCOECRYJRG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  7.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-n-hexadecyl-4-[4-N,N-(dimethylamino)styryl]pyridinium bromide 在 cethyltrimethylammonium permanganate 作用下， 以 氯仿 为溶剂， 生成 对二甲氨基苯甲醛 、
  参考文献：
  名称：

  高锰酸根离子氧化苯乙烯基吡啶鎓染料

  摘要：

  N-烷基取代的苯乙烯基溴化溴化物在 KMnO4 和十六烷基三甲基高锰酸铵 (CTAP) 中的氧化导致形成相应的取代苯甲醛。水介质中的氧化由酸催化，而在氯仿介质中，反应在中性条件下进行。然而，反应在两种介质中通过相同的机制进行。KMnO4 在水介质中的氧化速度比 CTAP 在氯仿介质中的氧化速度快，这已通过疏水作用合理化。总速率方程可以表示为水介质中的速率 = k[底物]1.5[氧化剂]-0.75，氯仿介质中的速率 = k[底物]0.5[氧化剂]-1。根据取代基效应，提出了在烯烃碳上具有低电子密度的过渡态。

  DOI：

  10.1246/bcsj.67.3289
• 作为产物：
  描述：

  4-甲基吡啶 在 哌啶 作用下， 反应 15.0h， 生成 1-n-hexadecyl-4-[4-N,N-(dimethylamino)styryl]pyridinium bromide
  参考文献：
  名称：

  Mishra, P. K.; Mishra, B. K.; Behera, G. B., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1988, vol. 27, # 10, p. 889 - 892

  摘要：

  DOI：

文献信息

• Dye–Surfactant Interaction: Role of an Alkyl Chain in the Localization of Styrylpyridinium Dyes in a Hydrophobic Force Field of a Cationic Surfactant (CTAB)
  作者：Amaresh Mishra、Sanjukta Patel、Rajani K. Behera、Bijaya K. Mishra、Gopa B. Behera

  DOI：10.1246/bcsj.70.2913

  日期：1997.12

  The interaction of a number of cationic dyes (I) with a varying number of methylene groups (Cn) in the alkyl chain attached to pyridyl nitrogen with a cationic surfactant (CTAB) assembly is reported. The binding constant of the dyes (C5 to C18) with the micelle have been calculated, and are found to increase with increasing carbon chain. A plot of the binding constant vs. the chain length shows a curve with a maximum for C16, which is attributed to a compatibility factor. From studies of the electronic and emission spectra it is proposed that a micelle has a hydrophobic force field and that the dyes are localized in various pockets of the field.

  报告了一些阳离子染料（I）与阳离子表面活性剂（CTAB）的相互作用，这些阳离子染料（I）的烷基链中有不同数量的亚甲基（Cn）连接到吡啶氮上的阳离子表面活性剂（CTAB）组件中。通过计算发现，染料（C5 至 C18）与胶束的结合常数随碳链的增加而增加。结合常数与链长的关系曲线显示，C16 的结合常数最大，这归因于相容性因素。通过对电子和发射光谱的研究，提出胶束具有疏水力场，染料被定位在力场的不同口袋中。
• Liquid-crystalline behaviors of lanthanide complexes containing hemicyanine
  作者：K.Z Wang、C.H Huang、G.X Xu、Q.F Zhou

  DOI：10.1016/0038-1098(95)00221-9

  日期：1995.7

  crystalline behaviors of four lanthanide complexes, (E)-N-hexadecyl-4-(2-(4-(dimethylamino)phenyl)ethylene)pyridinium tetrakis(1-phenyl-3-methyl-4-benzoyl-5-pyrazolonato)lanthanide(La, Nd, Dy and Yb)(III) have been investigated by using differential scanning calorimetry (DSC), thermogravimetric and differential thermal analysis (TG-DTA) and polarized optical microscopy. Except for the lanthanum complex, the

  四种镧系元素配合物(E)-N-十六烷基-4-(2-(4-(二甲氨基)苯基)亚乙基)吡啶鎓四(1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮)的液晶行为）镧系元素（La、Nd、Dy 和 Yb）(III) 已通过使用差示扫描量热法 (DSC)、热重和差热分析 (TG-DTA) 以及偏光显微镜进行了研究。除镧络合物外，其他三种络合物均表现出具有典型近晶镶嵌结构的介晶行为。这是自发现取代双（酞菁）镥的圆盘状中间相以来，关于镧系金属晶体的第二份报告。
• Near-infrared photoluminescence of lanthanide complexes containing the hemicyanine chromophore
  作者：Rik Van Deun、Peter Nockemann、Tatjana N. Parac-Vogt、Kristof Van Hecke、Luc Van Meervelt、Christiane Görller-Walrand、Koen Binnemans

  DOI：10.1016/j.poly.2007.08.005

  日期：2007.11

  nato) lanthanide(III) complexes are described. These three complexes, containing trivalent neodymium, erbium and ytterbium, respectively, show near-infrared luminescence in acetonitrile solution upon UV irradiation. Luminescence decay times have been measured. The complexes consist of a positively charged hemicyanine chromophore with a long alkyl chain and a tetrakis(pyrazolonato) lanthanide(III) anion

  三个（E）-N-十六烷基-N '，N的近红外发光特性描述了′-二甲基氨基-噻唑四（1-苯基-3-甲基-4-苯甲酰基-5-吡唑并萘基）镧系元素（III）配合物。这三种分别包含三价钕，和的配合物在紫外线照射下在乙腈溶液中显示出近红外发光。已经测量了发光衰减时间。配合物由带有长烷基链的带正电的半菁发色团和四（吡唑并萘）镧系元素（III）阴离子组成。由于在吡唑并酮配体中不存在α-氢原子，并且由于配体球被四个双齿配体饱和，因此与例如喹啉酸酯配合物相比，发光性能得到增强。
• Reversal in solvatochromism in some novel styrylpyridinium dyes having a hydrophobic cleft
  作者：Mallika Panigrahi、Sukalyan Dash、Sabita Patel、P.K. Behera、B.K. Mishra

  DOI：10.1016/j.saa.2006.12.057

  日期：2007.11

  The influence of solvent polarity on the electronic transition of four different N-hexadecyl styrylpyridinium dyes has been investigated in 15 solvents. The E-T(30) scale has been used to propose a quantitative approach towards the relative stability of the electronic ground and excited state species. The extents of contribution of dipolar aprotic solvents towards the solvation of the excited species have been determined to be 42-48% for some of the dyes. Instead of a steady solvatochromism, all the dyes suffer a reversal in solvatochromism. The transitions of the solvatochromism, referred to as solvatochromic switches, are found to be at E-T(30) values of similar to 50 for methyl and N,N-dimethylamino substituted dyes while at 37.6 for hydroxyl substituted dye and similar to 45 for 4-(1-methyl-2-phenylethenyl) pyridinium dye. A reversal in the trend of solvent effect in the later dye corresponding to 4-(4-methyl styryl)pyridinium dye has been attributed to an analogy of series and parallel electron flow. (C) 2007 Elsevier B.V. All rights reserved.
• Langmuir Film-Forming and Second Harmonic Generation Properties of Lanthanide Complexes
  作者：Chunhui Huang、Kezhi Wang、Guangxian Xu、Xinsheng Zhao、Xiaoming Xie、Yu Xu、Yunqi Liu、Lingge Xu、Tiankai Li

  DOI：10.1021/j100039a029

  日期：1995.9

  A series of amphiphilic lanthanide complexes were designed and synthesized, in which the lanthanide complex anions act both as the counterions of hemicyanine and as the spacer within a Langmuir-Blodgett (LB) film. Studies on the surface pressure-area (pi-A) isotherms of these complexes show that the film-forming properties can be clearly improved if appropriate beta-diketone ligands were chosen. The effects of molecular structures of the complexes, including the variation of lanthanide central ions, the structures of beta-diketone ligands, and the length of alkyl chains in hemicyanines, on the film-forming properties of the materials are discussed. From second-harmonic generation experiments, the largely enhanced second-order molecular hyperpolarizability of lanthanide complexes with good film-forming properties were obtained compared with the hemicyanine iodide. This effect may be due in part to the local field effect but primarily molecular ordering and ordered segregation of hemicyanine chromophores by the bulky lanthanide complex anions. The charge separation of the hemicyanine chromophores was supported by the crystal structure of a model complex. The homogeneity of the film was verified by low angle X-ray diffraction and also by the linear relationship of the absorbance vs the number of layers of the LB films of a selected complex.