2-{2-[4-(dimethylamino)phenyl]vinyl}-1,3-dimethyl-1H-3,1-benzimidazol-3-ium iodide | 21337-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-{2-[4-(dimethylamino)phenyl]vinyl}-1,3-dimethyl-1H-3,1-benzimidazol-3-ium iodide
• 英文别名: 2-{2-[4-(dimethylamino)phenyl]vinyl}-1,3-dimethyl-1H-benzimidazol-3-ium iodide salt；2-[2-(4-dimethylaminophenyl)vinyl]-1,3-dimethyl-3H-benzoimidazol-1-ium iodide；4-[2-(1,3-dimethylbenzimidazol-3-ium-2-yl)ethenyl]-N,N-dimethylaniline;iodide
• CAS: 21337-25-7
• 化学式: C₁₉H₂₂N₃*I
• 分子量: 419.308
• InChiKey: BCQPLBHDCAKAOQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  12
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2,3-trimethylbenzimidazolium iodide 、 对二甲氨基苯甲醛 在 哌啶 作用下， 反应 4.0h， 以70%的产率得到2-{2-[4-(dimethylamino)phenyl]vinyl}-1,3-dimethyl-1H-3,1-benzimidazol-3-ium iodide
  参考文献：
  名称：

  A small-molecule with a large two-photon absorption cross-section serves as a membrane-permeable ribonucleic acid (RNA) probe for live cell imaging

  摘要：

  DMI可以在活体系统中点亮细胞核和细胞质的RNA，不仅具有更大的双光子吸收截面（981 GM），而且显示出对活跃细胞的质膜具有高渗透性。

  DOI：

  10.1039/c8nj02425a

文献信息

• 一种RNA成像的双光子荧光探针及其在活细 胞中的应用
  申请人：山东省科学院新材料研究所

  公开号：CN106496126B

  公开（公告）日：2019-05-28

  本发明涉及一种RNA成像的双光子荧光探针及其在活细胞中的应用，探针结构通式如(I)所示：其中：R为氢、烷基、羟烷基或醚基；X为溴或碘。本发明双光子荧光探针是一类新型的RNA选择性识别的双光子荧光探针，该探针具有膜通透性好、显色强、光稳定性好的特点，可开发为RNA相关的生理、病理学研究用生物检测试剂。
• Application of spectroscopic and theoretical methods in the studies of photoisomerization and photophysical properties of the push—pull styryl-benzimidazole dyes
  作者：B. Jędrzejewska、B. Ośmiałowski、R. Zaleśny

  DOI：10.1039/c5pp00361j

  日期：2016.1

  and fluorescence band positions are affected by the character of the substituent and by the solvent polarity. The fluorescence decay of the dyes shows two lifetimes interpreted in terms of emission from two forms of the dye in the excited state. Moreover, the photochemical trans→cis isomerization is reported for these compounds. It occurs from the first excited singlet state of the trans isomer to the

  描述和讨论了一系列取代的1,3-二甲基-2-氨基苯乙烯基苯并咪唑碘化物的合成和光谱性质。产物通过NMR，IR和UV-Vis光谱法和元素分析鉴定。它们的电子吸收和荧光带位置受取代基的特性和溶剂极性的影响。染料的荧光衰减显示出两种寿命，这是从两种形式的处于激发态的染料发出的光来解释的。此外，据报道这些化合物的光化学反式→顺式异构化。它在反式S0→S1激发后从反式异构体的第一个激发单线态到顺式异构体发生。苯乙烯部分中取代基的供电子特性是影响光异构化过程的关键因素之一。顺式异构体的结构通过（1）H和（15）N NMR确定。量子化学计算的结果支持了实验研究。
• Smith, Journal of the Chemical Society, 1923, vol. 123, p. 2294
  作者：Smith

  DOI：——

  日期：——
• Studies of 2-azaazulenium derivatives – 3: The nature of electron transitions and spectral properties of styryl dyes containing terminal groups of different types
  作者：Julia L. Bricks、Alona V. Stanova、Aleksey B. Ryabitsky、Valeriy M. Yashchuk、Aleksey D. Kachkovsky

  DOI：10.1016/j.molstruc.2012.08.034

  日期：2013.2

  This paper presents the results of a quantum-chemical study of the molecular geometry and electron structure as well as spectral measurements of absorption and C-13 NMR spectra of dimethylaminostyryls, methoxystyryls, and methylstyryls bearing 2-azaazlenium (AA) moiety in comparison with analogous dyes containing 2-benzimidazolim and 4-pyrylium residues. Based on the analysis of both calculations and experimental data, it was concluded that these types of extremely unsymmetrical cyanines differ between each other only slightly in the ground state with respect to the charge distribution and molecular geometry while their spectral properties reveal a considerable difference between dimethylaminostyryls and methoxystyryls due to the lowest disposition of the lone electron pair level of the oxygen atom and hence, limiting basicity of the p-methoxyphenylene residue. It was shown that appearance of a high-positioned local level generated by AA terminal group caused the inversion of the delocalized and quasi-local electron transitions in AA-methoxystyryl and hence drastic changes in its absorption spectrum. (C) 2012 Elsevier B.V. All rights reserved.