Metalloaromatic species are unique and important both experimentally and theoretically. Significant progress has been made during the past few decades. New aromatic systems have challenged and extended the concept of aromaticity remarkably. In this perspective, recent results on the study of the dianion aromatic metalloles and their corresponding analogues are reviewed. These include the dilithio group 14 metalloles, group 13 metalloles and transition metal metalloles. X-ray crystallography has made a key contribution to the understanding of the structures. Various theoretical tools, such as NICS and AdNDP, make it possible to measure the aromaticity beyond Hückel’s rule. The dianion butadiene skeletons play a key role in these metalloles and can be regarded as non-innocent ligands, which accept the electrons from the metal center and thus form the aromatic rings. By simply changing the central metals to different metals, the metallole analogues such as dicupra[10]annulenes and spiroaromatic palladoles can also be generated, which opens a door to synthesize other metalla-macrocyclic aromatics. Key challenges and envisioned opportunities for the future, such as applying these dianion metalloles as novel ligands of transition metals and generating new types of organometallic aromatic system, are also discussed.

中文翻译：

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芳香族双阴离子金属醇

金属芳香族物质在实验和理论上都是独特而重要的。在过去的几十年中取得了重大进展。新的芳香系统显着挑战和扩展了芳香性的概念。从这个角度，回顾了最近关于双阴离子芳族金属及其相应类似物的研究成果。这些包括二硫代第 14 族金属化合物、第 13 族金属化合物和过渡金属金属化合物。X 射线晶体学对理解结构做出了重要贡献。各种理论工具，如 NICS 和 AdNDP，使得测量超出 Hückel 规则的芳香性成为可能。二阴离子丁二烯骨架在这些金属分子中起关键作用，可被视为非无害配体，它接受来自金属中心的电子，从而形成芳环。通过简单地将中心金属换成不同的金属，还可以生成二铜[10]环烯和螺芳环芳烃等金属醇类似物，为合成其他金属-大环芳烃打开了大门。还讨论了未来的关键挑战和设想的机遇，例如将这些双阴离子金属化合物用作过渡金属的新型配体和生成新型有机金属芳烃体系。