2-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium iodide | 150623-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium iodide
• 英文别名: 2-[(1E,3E)-4-(4-dimethylaminophenyl)-1,3-butadienyl]-1,3,3-trimethyl-3H-indolium iodide；N,N-dimethyl-4-[4-(1,3,3-trimethylindol-1-ium-2-yl)buta-1,3-dienyl]aniline;iodide
• CAS: 150623-58-8
• 化学式: C₂₃H₂₇N₂*I
• 分子量: 458.385
• InChiKey: WUBGMBIWICKMIS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2,3,3-四甲基-3H-吲哚鎓碘化物 、 4-二甲基氨基肉桂醛 以 乙醇 为溶剂， 生成 2-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium iodide
  参考文献：
  名称：

  基于Indolium衍生物的酪蛋白识别和定量的OFF / ON红光荧光探针

  摘要：

  合成了含有不同电子供体基团（H1-H5）的5种2、3、3-三甲基-3H-吲哚衍生物，用于蛋白质的测定。发现了H3，一种敏感的发红光荧光探针，用于区分疏水性蛋白质和亲水性蛋白质。H3的OFF-ON荧光开关是由于在水性缓冲液中与疏水蛋白结合时形成的扭曲分子内电荷转移（TICT）状态引起的。H3的发射强度与酪蛋白浓度（r = 0.9989）。在此基础上，开发了一种新型酪蛋白定量测定方法，并将该方法用于奶粉样品中酪蛋白的测定。成功地，结果与Biuret方法非常吻合。此外，由于三种酪蛋白组分（α-，β-和κ-酪蛋白）与H3探针的结合常数相差很大，因此建立了一种简单而灵敏的方法来区分和定量三种酪蛋白组分。

  DOI：

  10.1007/s10895-016-1967-0

文献信息

• The synthesis, structure and spectral properties of new long-wavelength benzodipyrroleninium-based bis-styryl dyes
  作者：Iryna A. Fedyunyayeva、Oleksii P. Klochko、Оlga M. Semenova、Sania U. Khabuseva、Yevgen A. Povrozin、Oksana O. Sokolyk、Olena Yu. Stepanenko、Ewald A. Terpetschnig、Leonid D. Patsenker

  DOI：10.1016/j.dyepig.2010.12.004

  日期：2011.8

  Novel bis-styryl dyes based on a quaternized centrosymmetrical benzodipyrrolenine moiety were synthesized by reaction of a quaternized benzodipyrrolenine with two equivalents of 4-dimethylaminobenzaldehyde, 4-dimethylaminocinnamoic aldehyde or 4-(3,5-diphenyl-4,5-dihydro-1H-1-pyrazolyl) benzaldehyde. The molecular structures and spectral properties of these dyes were investigated using PM3 and PPP CI quantum chemical simulations and compared with biscyanines and parent "monomeric" styryl dyes. Conjugation of two uniform "monomeric" styryl chromophores to form a bis-chromophoric system was found to cause a pronounced red-shift (similar to 100 nm) of the absorption and emission maxima, an increase of the extinction coefficients but also a conformational rigidization of the molecules. This results in better vibrationally resolved absorption and emission bands and, in general, in increased quantum yields. Bis-styryl dyes absorb and emit in the red and near-IR spectral region (643-812 nm). They have high extinction coefficients (<= 133,000 M-1 cm(-1)), large Stokes' shifts (up to 55 nm in chloroform and 90 nm in methanol), and quantum yields in chloroform <= 10%, whereas polar solvents decrease quantum yields. Despite their symmetrical structures these bis-styryl dyes exhibit spectral properties in solvents of different polarity that are more resemble those of unsymmetrical "monomeric" styryls. (C) 2010 Elsevier Ltd. All rights reserved.