基于 4-(芳基)-苯并[4,5]咪唑并[1,2-]嘧啶-3-甲腈的荧光团：Povarov 反应合成、光物理研究和 DFT 计算。

4-(Aryl)-Benzo[4,5]imidazo[1,2-]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations.

机构信息

Chemical Engineering Institute, Ural Federal University, 19 Mira St., 620002 Yekaterinburg, Russia.

Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, Russia.

出版信息

Molecules. 2022 Nov 19;27(22):8029. doi: 10.3390/molecules27228029.

A series of novel 4-(aryl)-benzo[4,5]imidazo[1,2-]pyrimidine-3-carbonitriles were obtained through the Povarov (aza-Diels-Alder) and oxidation reactions, starting from benzimidazole-2-arylimines. Based on the literature data and X-ray diffraction analysis, it was discovered that during the Povarov reaction, [1,3] sigmatropic rearrangement leading to dihydrobenzimidazo[1,2-]pyrimidines took place. The structures of all the obtained compounds were confirmed based on the data from H- and C-NMR spectroscopy, IR spectroscopy, and elemental analysis. For all the obtained compounds, their photophysical properties were studied. In all the cases, a positive emission solvatochromism with Stokes shifts from 120 to 180 nm was recorded. Aggregation-Induced Emission (AIE) has been illustrated for compound using different water fractions (fw) in THF. The compounds and demonstrated changes in emission maxima or/and intensities after mechanical stimulation.

一系列新型 4-(芳基)-苯并[4,5]咪唑并[1,2-]嘧啶-3-甲腈是通过 Povarov（aza-Diels-Alder）和氧化反应，从苯并咪唑-2-芳基亚胺出发得到的。根据文献数据和 X 射线衍射分析，发现[1,3]σ重排导致二氢苯并咪唑并[1,2-]嘧啶的发生。所有得到的化合物的结构都基于 H-和 C-NMR 光谱、IR 光谱和元素分析的数据得到确认。对所有得到的化合物，都研究了它们的光物理性质。在所有情况下，都记录到了具有 120 至 180nm 斯托克斯位移的正发射溶剂化变色。使用不同的水分数 (fw) 在 THF 中，用化合物说明了聚集诱导发射 (AIE)。化合物和在机械刺激后表现出发射最大值或/和强度的变化。