(E)-1-methyl-4-[4-amino-styryl] pyridinium iodide | 139619-03-7

• 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)-1-methyl-4-[4-amino-styryl] pyridinium iodide
• 英文别名: 1-methyl-4-pyridinium iodide；4-(4-aminostyryl)-1-methylpyridin-1-ium iodide；4-[2-(1-methylpyridin-1-ium-4-yl)ethenyl]aniline;iodide
• CAS: 139619-03-7
• 化学式: C₁₄H₁₅N₂*I
• 分子量: 338.191
• InChiKey: SMVFACSHTHORCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.9
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-1-methyl-4-[4-amino-styryl] pyridinium iodide 在 六氟磷酸银 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到4-(4-aminostyryl)-1-methylpyridin-1-ium hexafluorophosphate
  参考文献：
  名称：

  Water-soluble small-molecule probes for RNA based on a two-photon fluorescence “off–on” process: systematic analysis in live cell imaging and understanding of structure–activity relationships

  摘要：

  L1-5对RNA的体内外显著双光子荧光响应表明氨基团和吡啶阳离子的协同效应。

  DOI：

  10.1039/c7cc07288k
• 作为产物：
  描述：

  trans-1-methyl-4-<4-nitrostyryl>-pyridinium iodide 在 hydrazine hydrate 、 palladium on activated charcoal 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以82%的产率得到(E)-1-methyl-4-[4-amino-styryl] pyridinium iodide
  参考文献：
  名称：

  Water-soluble small-molecule probes for RNA based on a two-photon fluorescence “off–on” process: systematic analysis in live cell imaging and understanding of structure–activity relationships

  摘要：

  L1-5对RNA的体内外显著双光子荧光响应表明氨基团和吡啶阳离子的协同效应。

  DOI：

  10.1039/c7cc07288k

文献信息

• Influence of solvent polarity and medium acidity on the UV–Vis spectral behavior of 1-methyl-4-[4-amino-styryl] pyridinum iodide
  作者：Samy A El-Daly、Mahmoud H Abdel-Kader、Raafat M Issa、El-Sayed A El-Sherbini

  DOI：10.1016/s1386-1425(02)00182-8

  日期：2003.1

  and excitation spectra of 1-methyl-4-[4-aminostyryl] pyridinum iodide (M-NH2) were measured in solvents of different polarity. The (M-NH2) dye exhibits negative solvatochromism, i.e. a hypsochromic band shift as the solvent polarity increases. The fluorescence quantum yield is also sensitive to the polarity and viscosity of the medium. The ground and excited state protonation constants were calculated

  在不同极性的溶剂中测量了1-甲基-4- [4-氨基苯乙烯基]碘化吡啶鎓碘化物（M-NH2）的电子吸收和激发光谱。（M-NH 2）染料表现出负溶剂溶变色，即随着溶剂极性的增加而发生的变色带移。荧光量子产率也对介质的极性和粘度敏感。计算出基态和激发态质子化常数，分别为3.35和0.62。在十二烷基硫酸钠（SDS）中也研究了胶束化对（M-NH2）发射光谱的影响。荧光强度随着SDS浓度的增加而增加，并在cmc处发生突变。还在pH 1.1的缓冲水溶液中测定了顺式反光异构化的量子产率。
• Azido Push−Pull Fluorogens Photoactivate to Produce Bright Fluorescent Labels
  作者：Samuel J. Lord、Hsiao-lu D. Lee、Reichel Samuel、Ryan Weber、Na Liu、Nicholas R. Conley、Michael A. Thompson、Robert J. Twieg、W. E. Moerner

  DOI：10.1021/jp907080r

  日期：2010.11.18

  Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine thus restoring charge-transfer absorption and fluorescence Previously we reported that one compound DCDHF-V-P-azide was photoactivatable Here we demonstrate that the azide-to amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield photostability and turn-on ratio Azido push-pull fluorogens provide a new class of photoactivatable single molecule probes for flourescent labeling and super-resolution microscopy Lastly we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling)
• Peesapati; Rao; Pethrick, Journal of the Indian Chemical Society, 1991, vol. 68, # 7, p. 389 - 392
  作者：Peesapati、Rao、Pethrick

  DOI：——

  日期：——