(5-anilino-2,4-pentadienylidene)anilinium chloride

• 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: (5-anilino-2,4-pentadienylidene)anilinium chloride
• 英文别名: N-[(1E,3E)-5-phenylimino-1,3-pentadienyl]aniline hydrochloride；N-((2E,4E)-5-anilinopenta-2,4-dienylidene)anilinium chloride；glutaconaldehyde dianil monohydrochloride；glutacondianil hydrochloride；N-((1E,3E)-5-(phenylimino)penta-1,3-dienyl)benzenamine hydrochloride；phenyl-[(1E,3E)-5-phenyliminopenta-1,3-dienyl]azanium;chloride
• 化学式: C₁₇H₁₆N₂*ClH
• 分子量: 284.788
• InChiKey: VUCMMJBDNXZQDJ-ZUJIUJENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-anilino-2,4-pentadienylidene)anilinium chloride 在 乙酸酐 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 1,3-dimethyl-5-[(2E,4E,6E)-6-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)hexa-2,4-dien-1-ylidene]pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Influence of the Sign of Solvatochromism of Merocyanines on their Photoelectric Properties in Polymer Films

  摘要：

  DOI：

  10.1023/b:japs.0000049621.08104.86
• 作为产物：
  描述：

  1-(trimethylsiloxy)-1,3-butadiene 、 苯胺 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 生成 (5-anilino-2,4-pentadienylidene)anilinium chloride
  参考文献：
  名称：

  Makin, S. M.; Kruglikova, R. I.; Lonina, N. N., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 627 - 629

  摘要：

  DOI：

文献信息

• Photophysical characterization and BSA interaction of the direct ring carboxy functionalized unsymmetrical NIR cyanine dyes
  作者：Maryala Saikiran、Daisuke Sato、Shyam S. Pandey、Takeshi Ohta、Shuzi Hayase、Tamaki Kato

  DOI：10.1016/j.dyepig.2017.01.015

  日期：2017.5

  owing to their enhanced dye aggregation. Interaction of these dyes with BSA leads to not only enhanced emission intensity but also bathochromically shifted absorption maximum due to formation of dye-BSA conjugate. These dyes bind strongly with BSA having about an order of magnitude higher binding constant as compared to the typical cyanine dyes. Amongst the unsymmetrical cyanine dyes investigated in this

  合成了具有直接-COOH官能化吲哚环的新型近红外（NIR）敏感的不对称花青染料，对其进行了表征和光物理研究。然后，对这些不对称的花青染料进行研究，以研究它们与磷酸盐缓冲溶液中作为模型蛋白的牛血清白蛋白（BSA）的相互作用。除了具有高摩尔消光系数的NIR吸收和发射外，由于其增强的染料聚集作用，它们在PBS溶液中显示出蓝移。这些染料与BSA的相互作用不仅导致发射强度增强，而且由于形成染料-BSA共轭物而导致红移最大吸收。与典型的花青染料相比，这些染料与BSA牢固地结合，其结合常数高约一个数量级。7  M -1。
• Synthesis and linear/nonlinear optical properties of a new class of ‘RHS’ NLO chromophore
  作者：Andrew J. Kay、Anthony D. Woolhouse、Yuxia Zhao、Koen Clays

  DOI：10.1039/b315274j

  日期：——

  Examples of a new class of zwitterionic, “right-hand side” merocyanines containing a cyanodicyanomethylidenedihydrofuran electron acceptor have been prepared. As well as allowing for the facile synthesis of these chromophores, our synthetic methodology enables considerable variation in both the donor moiety as well as the extent of conjugation between the donor and acceptor systems. As expected, all of these “right-hand side” systems are negatively solvatochromic, with the difference between λmax (polar vs. nonpolar solvents) increasing with the extent of conjugation. In accord with expectations, hyper-Raleigh scattering (HRS) measurements confirm that molecules with the greatest conjugation pathway (for e.g.21c, 23c) have the largest first hyperpolarisabilites, βo. In addition, our HRS evaluation indicates that the 4-quinolinylidene donor nucleus is superior to both the 4-pyridinylidene and benzothiazolylidene systems. The figures of merit, μ(calc).βo(measured), that we obtain for some of these compounds, are of a similar magnitude to the best “left hand side” examples reported in the literature. In order to demonstrate the versatility of our synthetic technique, representative polymer-tetherable derivatives of these compounds have been prepared, as have the corresponding TDI-based polyurethanes.

  已经制备出一种新的双离子型“右侧”梅罗氰胺类化合物，其包含氰基二氰甲基二氢呋喃电子受体。我们的合成方法不仅允许这些色素的简便合成，还能在供体部分及供体与受体系统之间的共轭程度上进行相当大的变化。正如预期的那样，所有这些“右侧”系统都表现出负溶剂色散性，最大波长（极性与非极性溶剂）之间的差异随着共轭程度的增加而增大。符合预期，超拉赖散射（HRS）测量证实，具有最大共轭路径的分子（例如21c、23c）具有最大的首个超极化率βo。此外，我们的HRS评估表明，4-喹啉基腈供体核优于4-吡啶基腈和苯并噻唑基腈系统。我们为一些化合物获得的绩效指标μ(calc)·βo(measured)与文献中报道的最佳“左侧”示例相似。为了展示我们合成技术的多样性，已经制备了这些化合物的代表性聚合物连接衍生物，以及相应的基于TDI的聚氨酯。
• Symmetric anionic polymethine dyes derived from fluorene and its derivatives with electron-acceptor substituents: synthesis and spectral properties
  作者：I. V. Kurdyukova、N. A. Derevyanko、A. A. Ishchenko、D. D. Mysyk

  DOI：10.1007/s11172-012-0040-7

  日期：2012.2

  Novel anionic polymethine dyes were synthesized from 2,7-bis(phenoxysulfonyl)-, 2,7-dinitro-, and 2,4,5,7-tetranitrofluorenes. The reasons for the complicated shape of their absorption spectra were analyzed: the formation of contact ion pairs, associates, and conformational isomers and electronic effects of substituents. The quantum chemical calculations by the Pariser—Parr—Pople method and nonempirical

  新型阴离子聚次甲基染料由 2,7-双(苯氧基磺酰基)-、2,7-二硝基-和 2,4,5,7-四硝基芴合成。分析了其吸收光谱形状复杂的原因：接触离子对、缔合体和构象异构体的形成以及取代基的电子效应。在 B3LYP/6-31G(d,p) 基组中，Pariser-Parr-Pople 方法和非经验 DFT 和 TDDFT 方法的量子化学计算表明，硝基的轨道与 SO2OPh 的轨道不同，是与常见的发色团系统有效共轭，诱导额外的电子跃迁。
• Synthesis and fluorescent characteristics of imidazole–indocyanine green conjugates
  作者：Christopher Pavlik、Nrusingh C. Biswal、Faith Corbo Gaenzler、Martha D. Morton、Liisa T. Kuhn、Kevin P. Claffey、Quing Zhu、Michael B. Smith

  DOI：10.1016/j.dyepig.2010.08.008

  日期：2011.4

  We have successfully synthesized imidazole-dye conjugates by linking imidazole and nitroimidazoleacetic acids to an indocyanine green (ICG) carboxylic acid derivative using an ethanolamine linker These dye-conjugates show absorbance peaks at 754-756 nm and fluorescence peaks at 780 rim The dye-conjugates show a blue shift of 25 nm and 30 nm in the absorption and fluorescence spectra respectively when compared to that of standard cardiogreen There is no change in absorption and fluorescence spectral profiles between the ICG derivative and imidazole conjugates The extinction coefficients of new ICG derivative and imidazole conjugates are 1 8 times higher than that of standard ICG The relative quantum yields of the new compounds are 4 5-5 5 times higher than that of the Sigma-Aldrich s ICG The dyes are tested for hypoxia in-vitro with 4T1 luc cell lines and it is found that the cells treated with 2-nitroimidazole ICG show a contrast of fluorescence signal of 2 5-30 for the cells under hypoxic to that of cells under normoxic However pure ICG shows no significant difference between hypoxic and normoxic cells (C) 2010 Elsevier Ltd All rights reserved