2-methyl-1,3-diphenylbenzimidazolium chloride | 28510-55-6

• 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-methyl-1,3-diphenylbenzimidazolium chloride
• 英文别名: 2-methyl-1,3-diphenyl-3H-benzimidazol-1-ium chloride；2-methyl-1,3-diphenylbenzimidazol-3-ium;chloride
• CAS: 28510-55-6
• 化学式: C₂₀H₁₇N₂*Cl
• 分子量: 320.821
• InChiKey: IOZQJWAPQAIAKO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  费舍尔氏醛 、 2-methyl-1,3-diphenylbenzimidazolium chloride 在 sodium ethanolate 、 乙酸酐 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以7.5%的产率得到1,3-Diphenyl-2-{(E)-3-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-propenyl}-3H-benzoimidazol-1-ium; iodide
  参考文献：
  名称：

  Ishchenko, A. A.; Zubarovskii, V. M.; Gromova, G. A., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 562 - 570

  摘要：

  DOI：

文献信息

• Deeply coloured and highly fluorescent dipolar merocyanines based on tricyanofuran
  作者：Nadezhda A. Derevyanko、Alexander A. Ishchenko、Andrii V. Kulinich

  DOI：10.1039/c9cp05827c

  日期：——

  TCF as the acceptor group of merocyanines, having its own extended π-system, gives access to deeply coloured dyes exhibiting good fluorescence efficiency in the red and near-IR spectral range.

  作为甲氰化物的受体基团，TCF具有自身的扩展π-体系，使得可以获得在红色和近红外光谱范围内表现出良好荧光效率的深色染料。
• Merocyanines based on 1,3-indanedione: electronic structure and solvatochromism
  作者：Andrii V. Kulinich、Nadia A. Derevyanko、Elena K. Mikitenko、Alexander A. Ishchenko

  DOI：10.1002/poc.1821

  日期：2011.8

  merocyanines derived from 1,3‐indanedione and heterocycles of various electron‐donating properties was studied in detail. Their solvatochromic properties were explored in a wide range of solvent polarities to reveal the dependences of their chromacity and electronic structure on the key structural parameters – the properties of a donor heterocycle and the polymethine chain length. Also the dyes were studied

  详细研究了一系列由1,3-茚满二酮和各种给电子性质的杂环衍生的花菁。在广泛的溶剂极性中探索了它们的溶剂变色性质，以揭示其色度和电子结构对关键结构参数（供体杂环的性质和聚次甲基链长）的依赖性。此外，还通过半经验AM1和非经验密度泛函理论/ B3LYP方法，通过NMR光谱和量子化学计算研究了染料。所探索染料的溶剂变色性质与衍生自丙二腈作为受体基团的部花菁的溶剂变色性质相当接近。仅在质子乙醇中观察到明显的区别。明显地，在1,3-茚满二酮衍生物的情况下，它们与溶剂-溶质氢键的形成有关。与已知的数据相反，即使在非质子溶剂中，1,3-茚满二酮的电子受体性能也比丙二腈强。在真空和溶剂基质中均进行了花菁分子轨道的分析和电子光谱的模拟，并对吸收电子跃迁进行了分析。计算了新的花菁和相应的阳离子和阴离子花青染料的静态非线性光学性质。版权所有©2010 John Wiley＆Sons，Ltd. 与已知的数据相反，
• Synthesis and spectral properties of malononitrile-based merocyanine dyes
  作者：A. V. Kulinich、N. A. Derevyanko、A. A. Ishchenko

  DOI：10.1007/s11172-006-0196-0

  日期：2005.12

  Di-, tetra-, and hexamethine merocyanines derived from malononitrile and heterocycles with moderate (dyes 1–6), strong (7–9), and weak (10 and 11) electron-releasing ability were synthesized. The electronic structures of merocyanines 10 and 11 are similar to the neutral polyene state, whereas those of 7–9 are similar to the ideal polymethine state. These tendencies become more pronounced with increasing length of the polymethine chain. The merocyanines derived from heterocyclic residues with weak or moderate electron-releasing ability exhibit a positive solvatochromism, whereas those with strong electron-releasing ability show a negative solvatochromism. An increase in the polarity of the solvent makes the former compounds more similar to polymethines, whereas the latter become more similar to polyenes bearing opposite charges on the end groups. The nature of the factors (nonspecific solvation, specific nucleophilic and electrophilic solvation, and vibronic interactions) responsible for the observed characteristic features was analyzed.

  合成了由美克腈和具有中等（染料1-6）、强（染料7-9）及弱（染料10和11）电子供给能力的杂环衍生的二甲、四甲和六甲美克腈。美克腈10和11的电子结构类似于中性聚烯状态，而7-9的电子结构则更接近理想的聚美烯状态。随着聚美烯链长的增加，这些趋势变得更加明显。由具有弱或中等电子供给能力的杂环残基衍生的美克腈表现出正溶剂色变，而那些具有强电子供给能力的则表现出负溶剂色变。溶剂极性的增加使得前者的化合物更类似于聚美烯，而后者则更类似于在末端基团带有相反电荷的聚烯。对导致观察到的特征特性的因素（非特异性溶剂化、特异性亲核和亲电子溶剂化以及振动耦合效应）进行了分析。
• Merocyanines based on 1,2-diphenyl-3,5-pyrazolidinedione
  作者：Heorhii V. Humeniuk、Nadezhda A. Derevyanko、Alexander A. Ishchenko、Andrii V. Kulinich

  DOI：10.1039/c9nj03275d

  日期：——

  5-pyrazolidinedione as the acceptor terminal group. Their absorption and fluorescence spectra have been studied in different polarity solvents. From the analysis of their solvatochromism, vinylene shifts, Brooker's deviations, and spectral band shapes, the effects of structural modifications, viz. the donor group strength and the polymethine chain length, on their electronic structures have been revealed

  已经合成了乙烯基系列的花菁，其中吲哚，苯并咪唑和苯并[ cd ]吲哚为供体末端，1,2-二苯基-3,5-吡唑烷二酮为受体端基。已经在不同极性的溶剂中研究了它们的吸收和荧光光谱。通过对它们的溶剂变色，亚乙烯基位移，Brooker偏差和光谱带形状的分析，可以看到结构修饰的影响。揭示了电子结构上的供体基团强度和聚次甲基链长。根据获得的数据，对1,2-二苯基-3,5-吡唑烷二酮残基的受体强度进行了重新评估，与文献数据相反，它不是一个记录力强的受体。使用PCM溶剂化模型，已在三种不同的溶剂中进行了所研究染料的（TD）-DFT / B3LYP计算。通过对TD-B3LYP电子跃迁的分析，所研究染料的低荧光性可以通过与位于分子轨道上的低位非荧光ππ*激发态相关的快速竞争性单分子非辐射衰变来解释。受体末端基团。
• Synthesis, structure, and solvatochromism of merocyanine dyes based on barbituric acid
  作者：A. V. Kulinich、N. A. Derevyanko、A. A. Ishchenko

  DOI：10.1134/s1070363206090167

  日期：2006.9

  Di-, tetra-, and hexamethinemerocyanines were synthesized on the basis of barbituric and 1,3-dimethylbarbituric acids and heterocycles characterized by a strong (1-benzyl-1,2-dihydrobenzo[cd]indole), medium (1,3-dihydro-1,3,3-trimethyl-2H-indole and 3-ethyl-2,3-dihydro-1,3-benzothiazole), and strong electron-donor power (1,3-diphenyl-2,3-dihydro-1H-benzirnidazole). Their solvatochromic properties were analyzed using both conventional parameters (absorption maxima and molar absorption coefficients) and centroids, oscillator strengths, widths, asymmetry and excess coefficients, and fine structure of the long-wave absorption bands, which were determined by mathematical processing (method of moments). A combination of these parameters unambiguously characterizes limiting electronic states of merocyanines (neutral polyene, polymethine, or charged polyene) responsible for the type of solvatochronism. Relations were found between solvatochromic properties, on the one hand, and donor-acceptor power of the terminal groups, length of the polymethine chain, and solvent nature, on the other. The difference in solvatochromism (up to reversal of sign) of merocyanines derived from barbituric acid and their analogs based on 1,3-dimethylbarbituric acid originates from both the difference in their electronic asymmetry and the ability of the NH groups in the former to participate in hydrogen bonding with proton-acceptor solvents.