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Homoconjugation and Tautomeric Isomerism in Triptycene-Fused Pyridylbenzimidazoles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-04-03 , DOI: 10.1021/acs.joc.4c00221 Giovanni Preda 1 , Riccardo Mobili 1 , Davide Ravelli 1 , Valeria Amendola 1 , Dario Pasini 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-04-03 , DOI: 10.1021/acs.joc.4c00221 Giovanni Preda 1 , Riccardo Mobili 1 , Davide Ravelli 1 , Valeria Amendola 1 , Dario Pasini 1
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The facile, metal-free synthesis and characterization of three new series of triptycene-fused pyridylbenzimidazoles are reported; such compounds possess an imidazole moiety fused within the benzene rings of the trypticene and a pyridine ring installed at position 2 of the imidazole rings. The position of the nitrogen atom of the pyridyl moiety linked to position 2 of the fused benzimidazole scaffold is systematically changed from the ortho to para position. The number of substituted blades bearing the pyridyl-substituted fused benzimidazole scaffolds has been increased from one to three. Such a library of compounds allowed us to evaluate the enhancement of two main effects: tautomeric isomerism and homoconjugation. The characteristic dynamic equilibrium between different isomers induced by prototropic tautomerization was examined by 1H nuclear magnetic resonance spectroscopy. By comparison of the photophysical properties of the new compounds with those of classical planar pyridylbenzimidazoles, the presence of the homoconjugation effect between the different triptycene blades was demonstrated. Fine details of the electronic structure of the new derivatives were unraveled by a computational analysis. The novel compounds can be employed for the construction of intriguing self-assembled supramolecular architectures.
中文翻译：
三蝶烯稠合吡啶基苯并咪唑的同源共轭和互变异构现象
报告了三个新系列三蝶烯稠合吡啶基苯并咪唑的简便、无金属合成和表征；此类化合物具有稠合在色烯的苯环内的咪唑部分和安装在咪唑环的2位上的吡啶环。连接到稠合苯并咪唑骨架的2位的吡啶基部分的氮原子的位置系统地从邻位变为对位。带有吡啶基取代的稠合苯并咪唑支架的取代叶片的数量已从一个增加到三个。这样的化合物库使我们能够评估两种主要效应的增强：互变异构现象和同源共轭。通过1 H 核磁共振波谱检查了由质子互变引起的不同异构体之间的特征动态平衡。通过将新化合物与经典平面吡啶基苯并咪唑的光物理性质进行比较，证明了不同三蝶烯叶片之间存在同共轭效应。通过计算分析揭示了新衍生物电子结构的细节。这些新型化合物可用于构建有趣的自组装超分子结构。
更新日期：2024-04-03
中文翻译：
三蝶烯稠合吡啶基苯并咪唑的同源共轭和互变异构现象
报告了三个新系列三蝶烯稠合吡啶基苯并咪唑的简便、无金属合成和表征；此类化合物具有稠合在色烯的苯环内的咪唑部分和安装在咪唑环的2位上的吡啶环。连接到稠合苯并咪唑骨架的2位的吡啶基部分的氮原子的位置系统地从邻位变为对位。带有吡啶基取代的稠合苯并咪唑支架的取代叶片的数量已从一个增加到三个。这样的化合物库使我们能够评估两种主要效应的增强：互变异构现象和同源共轭。通过1 H 核磁共振波谱检查了由质子互变引起的不同异构体之间的特征动态平衡。通过将新化合物与经典平面吡啶基苯并咪唑的光物理性质进行比较，证明了不同三蝶烯叶片之间存在同共轭效应。通过计算分析揭示了新衍生物电子结构的细节。这些新型化合物可用于构建有趣的自组装超分子结构。
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