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Direct synthesis of gold(III)-annulated perylene diimides via multiple C–H aurations
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-06-21 , DOI: 10.1039/d4qo01075b
Wei Chen 1 , Qing-Yu Yang 1 , Kongchuan Wu 1 , Jianbin Lin 1 , Hui-Jun Zhang 1
Affiliation  

GA1We present a direct synthesis of novel gold(III)-annulated perylene diimides (Au-PDIs and Au2-PDIs) from ortho-pyridyl-substituted PDIs, achieving facile auration of two or four C–H bonds in one pot. Au2-PDI 12 (λmax = 635 nm) emerged as the most red-shifted compound among all reported heteroannulated PDIs. Cyclic voltammetry and density functional theory calculations indicate degenerated LUMO levels and substantial narrowing of the HOMO–LUMO energy gaps. This synthetic strategy is expected to unlock the potential of diverse transition metal-annulated PDIs.

中文翻译:


通过多重C-H原子直接合成金(III)环苝二酰亚胺



GA1我们提出了一种从邻位吡啶基取代的 PDI 直接合成新型金(III)环化苝二酰亚胺(Au-PDI 和 Au 2 -PDI)的方法,实现了两个或四个 C-H 键的轻松合成在一个锅里。 Au 2 -PDI 12 (λ max = 635 nm) 是所有报道的杂环 PDI 中红移最大的化合物。循环伏安法和密度泛函理论计算表明 LUMO 能级退化并且 HOMO-LUMO 能隙显着变窄。这种合成策略有望释放多种过渡金属环化 PDI 的潜力。
更新日期:2024-06-21
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