3-dicyanomethylene-4-[((1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylidene)]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]-cyclobut-1-en-1-olate

• 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: 3-dicyanomethylene-4-[((1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylidene)]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]-cyclobut-1-en-1-olate
• 英文别名: [2-cyano-2-[(4Z)-3-oxo-4-[(1,3,3-trimethylindol-1-ium-2-yl)methylidene]-2-[(E)-(1,3,3-trimethylindol-2-ylidene)methyl]cyclobuten-1-yl]ethenylidene]azanide
• 化学式: C₃₁H₂₈N₄O
• 分子量: 472.59
• InChiKey: SUNWMKBAAZYSJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-butoxy-4-(1,3,3-trimethyl-3H-indol-2-ylidenemethyl)-3-cyclobutene-1,2-dione 以 乙醇 、 甲苯 、 正丁醇 为溶剂， 反应 120.0h， 生成 3-dicyanomethylene-4-[((1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylidene)]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]-cyclobut-1-en-1-olate
  参考文献：
  名称：

  Synthesis, characterization and protein-association of dicyanomethylene squaraine dyes

  摘要：

  We prepared several new dicyanomethylene squaraine dyes derived from indolenine, benzothiazole and benzoselenazole, with different substituent groups. All the obtained dyes display intense and narrow absorption bands and bright fluorescence emission in the Vis/NIR region (665-716 nm) when dissolved in organic solvents, especially for the unsymmetrical dyes containing sulphur and selenium atoms.The use of synthesized squaraine dyes as fluorescent probes for detection of bovine serum albumin (BSA) and human serum albumin (HSA) was explored in Tris-HCI buffer solutions. We observed that all the dyes are non-emissive in buffer solution but become fluorescent in the presence of BSA or HSA proteins, with the emission intensity increasing proportionally to the protein concentration (0.00-1.22 mu M). The most pronounced effect was observed for the symmetrical squaraine having two moieties of indolenine. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2017.07.070

文献信息

• Molecular structure and spectral properties of indolenine based norsquaraines versus squaraines
  作者：Olga S. Kolosova、Svitlana V. Shishkina、Vered Marks、Gary Gellerman、Iryna V. Hovor、Anatoliy L. Tatarets、Ewald A. Terpetschnig、Leonid D. Patsenker

  DOI：10.1016/j.dyepig.2018.12.007

  日期：2019.4

  dyes, wherein the oxygen of the squaric acid bridge was substituted with a barbituric or a dicyanomethylene group, were synthesized and their molecular structure, spectral and luminescent properties were compared to those of analogous squaraine dyes. The molecular structure was investigated using X-ray analysis, NMR spectroscopy and ab initio DFT B3LYP/6-311G (d, p) simulations. The calculated populations

  合成了新的基于吲哚烯胺的去甲鸟嘌呤染料，其中方酸桥的氧被巴比妥基或二氰基亚甲基取代，并且将它们的分子结构，光谱和发光性质与类似的方酸方块染料进行了比较。使用X射线分析，NMR光谱和从头算DFT B3LYP / 6-311G（d，p）模拟研究了分子结构。发现可能的构象体总数和内部旋转的障碍与实验数据高度吻合。Norsquarain吸收和发射与相应的quaqua相同的长波长光谱范围内的光，但归因于分子内H-键和增加的构象刚度，它们对溶剂极性和蛋白质（BSA）的敏感性较低。