(E)-N-n-dodecyl-4-(2-(4(dimethylamino)phenyl)ethenyl)pyridinium bromide | 155888-02-1

• 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: (E)-N-n-dodecyl-4-(2-(4(dimethylamino)phenyl)ethenyl)pyridinium bromide
• 英文别名: 4-[2-(1-dodecylpyridin-1-ium-4-yl)ethenyl]-N,N-dimethylaniline;bromide
• CAS: 155888-02-1
• 化学式: Br*C₂₇H₄₁N₂
• 分子量: 473.54
• InChiKey: JFLCKNJNJKJAFQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  dysprosium nitrate 、 (E)-N-n-dodecyl-4-(2-(4(dimethylamino)phenyl)ethenyl)pyridinium bromide 、 4-苯甲酰基-3-甲基-1-苯基-2-吡唑-5-酮 以 乙醇 、 水 为溶剂， 生成 A12Dy(PMBP)4
  参考文献：
  名称：

  Langmuir Film-Forming and Second Harmonic Generation Properties of Lanthanide Complexes

  摘要：

  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.

  DOI：

  10.1021/j100039a029
• 作为产物：
  描述：

  4-甲基吡啶 在 哌啶 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 48.0h， 生成 (E)-N-n-dodecyl-4-(2-(4(dimethylamino)phenyl)ethenyl)pyridinium bromide
  参考文献：
  名称：

  Styrylpyridinium Derivatives for Fluorescent Cell Imaging

  摘要：

  为了研究苯乙烯吡啶（SP）化合物的光谱和细胞标记特性，我们合成了一组苯乙烯吡啶（SP）化合物。这些化合物由不同的电子捐赠部分（julolidine、对二甲氨基苯基、对甲氧基苯基、3,4,5-三甲氧基苯基）、共轭连接体（乙烯基、二乙烯基）和一个电子抽离的 N-烷基吡啶鎓部分组成。合成了在 1,3-三亚甲基单元上含有两个苯乙烯基吡啶鎓（双-SP）分子的双原子或双原子化合物。由二乙烯基连接体和强电子供体部分组成的化合物在近红外区域（约 760 纳米处为最大值）具有强烈的荧光。这些化合物对癌细胞系 HT-1080 和 MH-22A 具有相当高的细胞毒性；同时，对 NIH3T3 成纤维细胞系的基础细胞毒性从有毒到有害不等。SP 化合物 6e 对细胞株 HT-1080 的 IC50 值为 1.0 ± 0.03 µg/mL，对 MH-22A 的 IC50 值为 0.4 µg/mL；然而，其基础毒性 LD50 为 477 mg/kg（有害）。这些化合物显示出较大的斯托克斯位移，其中 6a,b 为 195 纳米，6e 为 240 纳米，6d 和 6c 分别为 325 纳米和 352 纳米。6a,b 的光量子产率（PLQY）值最高，分别为 15.1% 和 12.2%。SP 衍生物 6d、e（具有一个茱莉烷基的衍生物）的光量子产率分别为 0.5% 和 0.7%。用化合物 6e 进行细胞染色时，发现细胞胞质中有强烈的荧光信号，而细胞核则没有被染色。SP 化合物 6e 具有自组装特性，可形成平均直径为 118 nm 的脂质体。所获得的有关近红外荧光探针的新数据有助于开发生物医学应用领域的生物相容性染料。

  DOI：

  10.3390/ph16091245

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。
• Pyridinium compounds
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0139440A2

  公开（公告）日：1985-05-02

  Pyridinium compounds containing a cation having the formula la or lb and a pharmaceutically acceptable cation are useful as pharmaceuticals, particularly as anti-fungal agents. In formulae la and Ib R1 is alkyl of at least 3 carbon atoms or aralkyl; R2 and R5 are hydrogen or various defined substituents; R3 and R4 are hydrogen or lower alkyl; Re and R7 are lower alkyl or aryl(lower)alkyl or R6 and R7 represent a group having formula II (where A is -(CH2)n-, O, S or NR8 where n is 0, 1 or 2 and R8 is lower alkyl) or a mono- or di- (lower alkyl) substitution product of a group having formula II.

  含有具有式 la 或 lb 的阳离子和药学上可接受的阳离子的吡啶鎓化合物可用作药物，特别是抗真菌剂。 在式 la 和 Ib 中，R1 是至少含有 3 个碳原子的烷基或芳烷基；R2 和 R5 是氢或各种定义的取代基；R3 和 R4 是氢或低级烷基；Re 和 R7 是低级烷基或芳基（低级）烷基或 R6 和 R7 代表具有式 II 的基团（其中 A 是-(CH2)n-、O、S 或 NR8，其中 n 是 0、1 或 2，R8 是低级烷基）或具有式 II 的基团的单-或双（低级烷基）取代产物。
• Aligned Inclusion of Hemicyanine Dyes into Silica Zeolite Films for Second Harmonic Generation
  作者：Hyun Sung Kim、Seung Mook Lee、Kwang Ha、Changsoo Jung、Yun-Jo Lee、Yu Sung Chun、Doseok Kim、Bum Ku Rhee、Kyung Byung Yoon

  DOI：10.1021/ja037772q

  日期：2004.1.1

  Silicalite-1 films (thickness = 400 nm) supported on both sides of glass plates (SL/G) were prepared, and hemicyanine dyes (HC-n) with different alkyl chain lengths (n, n = 3, 6, 9, 12, 15, 18, 22, and 24) were included into the silicalite-1 films by dipping SL/Gs into each methanol solution of HC-n (1 mM) for 1 d. The included numbers of HC-n per channel (N-c) generally decreased with increasing n; that is, they were 6.4, 23.1, 15.4, 8.2, 5.7, 3.5, 0.9, and 1.2 molecules per channel, respectively. The d(33) value gradually increased with increasing n but decreased when n > 18; that is, they were 1.12, 0.50, 2.25, 3.59, 4.99, 5.30, 1.71, and 2.57 pm V-1, respectively. However, d(33)/N-c progressively increased with increasing n. The d(31) values were similar to100 times smaller than the corresponding d33 values, and the average d(33)/d(31) ratio was 109, which is higher than those of Langmuir-Blodgett (LB) films and poled polymers of nonlinear optical (NLO) dyes, by similar to2-5 and similar to30-50 times, respectively. The estimated average tilted angle of the dyes with respect to the channel direction was 7.7degrees, and the calculated average order parameter was 0.97, which is similar to480 times higher than the values observed from poled polymers. The degree of uniform alignment (DUA) generally increased with increasing n. The progressive increase of both DUA and d33/Nc with n is attributed to the increase in the tendency of HC-n to enter hydrophobic silicalite-1 channels with the hydrophobic alkyl chain first. A more than 134-fold increase in DUA was observed upon increasing n from 6 to 24. The DUA of HC-24 in the silicalite-1 film reached close to 1. Although the observed d33 values were lower than those of the LB films of NLO dyes due to very small dye densities of the silicalite films, this methodology bears a great potential to be developed into the methods for preparing practically viable NLO films.
• US4608379A
  申请人：——

  公开号：US4608379A

  公开（公告）日：1986-08-26