4-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-1-octadecylpyridinium bromide | 125851-04-9

• 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: 4-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-1-octadecylpyridinium bromide
• 英文别名: trans-(E)-N-octadecyl-4-(N',N'-dimethylamino)stilbazoliumbromide；4-{2-[4-(dimethylamino)phenyl]-ethenyl}-N-octadecylpyridiniumbromide；N,N-dimethyl-4-[2-(1-octadecylpyridin-1-ium-4-yl)ethenyl]aniline;bromide
• CAS: 125851-04-9
• 化学式: Br*C₃₃H₅₃N₂
• 分子量: 557.701
• InChiKey: JPILBZAQSAEVRX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  4-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-1-octadecylpyridinium bromide 在 sodium perchlorate 作用下， 以 乙醇 为溶剂， 以83%的产率得到4-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-1-octadecylpyridinium perchlorate
  参考文献：
  名称：

  基于苯乙烯染料的分子转子。分子碎片旋转的粘度依赖性

  摘要：

  合成了三种供体-受体苯乙烯基染料 R-Het+-CH=CH-C6H4-NR'R″ClO4-（Het 是吡啶基）。它们的光谱发光行为允许将它们分配给一类分子转子。研究了介质的粘度、极性和温度对其吸收和荧光特性的影响。随着介质粘度的增加和温度的降低，观察到染料荧光的显着增强，伴随着荧光最大值的短波长偏移。聚甲基丙烯酸甲酯薄膜中染料在 293 和 77 K 下的荧光光谱测量证实了介质粘度对光激发时分子碎片旋转能力的影响。根据量子化学计算，在非极性溶剂中苯乙烯染料的激发分子中，分子片段主要围绕中心乙烯键 $(HC\underline \cdots CH)$ 旋转。在极性溶剂中，围绕乙烯片段普通键的旋转势垒会降低。

  DOI：

  10.1007/s11172-014-0660-1
• 作为产物：
  描述：

  硬脂基溴 、 4-(4-(二甲氨基)苯乙烯基)吡啶 反应 4.0h， 以82%的产率得到4-{(E)-2-[4-(dimethylamino)phenyl]vinyl}-1-octadecylpyridinium bromide
  参考文献：
  名称：

  基于苯乙烯染料的分子转子。分子碎片旋转的粘度依赖性

  摘要：

  合成了三种供体-受体苯乙烯基染料 R-Het+-CH=CH-C6H4-NR'R″ClO4-（Het 是吡啶基）。它们的光谱发光行为允许将它们分配给一类分子转子。研究了介质的粘度、极性和温度对其吸收和荧光特性的影响。随着介质粘度的增加和温度的降低，观察到染料荧光的显着增强，伴随着荧光最大值的短波长偏移。聚甲基丙烯酸甲酯薄膜中染料在 293 和 77 K 下的荧光光谱测量证实了介质粘度对光激发时分子碎片旋转能力的影响。根据量子化学计算，在非极性溶剂中苯乙烯染料的激发分子中，分子片段主要围绕中心乙烯键 $(HC\underline \cdots CH)$ 旋转。在极性溶剂中，围绕乙烯片段普通键的旋转势垒会降低。

  DOI：

  10.1007/s11172-014-0660-1

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。
• 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.
• Stilbazolium dyes containing rare-earth ions
  作者：Koen Binnemans

  DOI：10.1016/s0925-8388(00)00618-6

  日期：2000.5

  The synthesis, thermal and spectroscopic properties of 28 rare-earth containing stilbazolium dyes are described. The complexes are prepared by reaction of the corresponding stilbazolium bromide (hemicyanine bromide) with a lanthanide salt and with a pyrazolone or a P-diketone. The bromide is replaced by a tetrakis pyrazolonato or by a tetrakis beta-diketonato lanthanide(III) counter ion. (C) 2000 Elsevier Science S.A. All rights reserved.