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Synthesis and derivatization of an isomer of an N-heterotriangulene bearing five-, six- and seven-membered rings around the central nitrogen atom
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-20 , DOI: 10.1039/d4qo02027h
Xinxin Chen, Weifan Wang, Gang Zhang

The functionalization of N-heterotriangulenes has been extensively investigated for their potential as optoelectronic materials. However, the study on the influence of molecular geometry on the properties of N-heterotriangulenes is still rare. Here we present the synthesis of an isomer of an N-heterotriangulene containing five-, six- and seven-membered rings around the central nitrogen atom. The isomer can be further derivatized by condensing with ortho-diamine compounds to extend the molecular conjugation. The photophysical and electrochemical properties of related compounds were characterized. The isomer bearing three carbonyl groups demonstrates room temperature phosphorescence, which is absent in the corresponding tert-butylated carbonyl-bridged N-heterotriangulene. Furthermore, the chemical oxidation of one of the isomers of the N-heterotriangulene to generate a cationic radical was also studied.

中文翻译:


N-异质三角烯异构体的合成和衍生化,该异构体在中心氮原子周围带有五元、六元和七元环



N-异质三角化合物的功能化因其作为光电材料的潜力而被广泛研究。然而,关于分子几何形状对 N-异质三角化合物性质影响的研究仍然很少见。在这里,我们介绍了 N-杂三角烯异构体的合成,该异构体在中心氮原子周围包含五元、六元和七元环。异构体可以通过与位二胺化合物缩合以延长分子偶联来进一步衍生化。对相关化合物的光物理和电化学性质进行了表征。带有三个羰基的异构体表现出室温磷光,而在相应的丁基化羰基桥 N-杂三角烯中不存在。此外,还研究了 N-杂三角烯的一种异构体的化学氧化生成阳离子自由基。
更新日期:2024-11-20
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