Abstract

Lithium ion-endohedral fullerene (Li⁺@C₆₀), a member of the burgeoning family of ion-endohedral fullerenes, holds substantial promise for diverse applications owing to its distinctive ionic properties. Despite the high demand for precise property tuning through chemical modification, there have been only a few reports detailing synthetic protocols for the derivatization of this novel material. In this study, we report the synthesis of Li⁺@C₆₀ derivatives via the thermal [2 + 2] cycloaddition reaction of styrene derivatives, achieving significantly higher yields of monofunctionalized Li⁺@C₆₀ compared to previously reported reactions. Furthermore, by combining experimental and theoretical approaches, we clarified the range of applicable substrates for the thermal [2 + 2] cycloaddition of Li⁺@C₆₀, highlighting the expanded scope of this straightforward and selective functionalization method.

Beilstein J. Org. Chem. 2024, 20, 653–660. doi:10.3762/bjoc.20.58

摘要

锂离子内嵌富勒烯 (Li ⁺ @C ₆₀ ) 是新兴的离子内嵌富勒烯家族的一员，由于其独特的离子特性，在多种应用中具有巨大的前景。尽管对通过化学修饰进行精确性能调节的需求很高，但只有少数报告详细介绍了这种新型材料的衍生化合成方案。在这项研究中，我们报道了通过苯乙烯衍生物的热[2+2]环加成反应合成Li ⁺ @C ₆₀衍生物，与之前报道的反应相比，单官能化Li ⁺ @C _{60的产率明显更高。此外，通过结合实验和理论方法，我们阐明了Li} ⁺ @C ₆₀热[2 + 2]环加成的适用底物范围，突出了这种简单且选择性功能化方法的扩展范围。

贝尔斯坦 J. 组织。化学。 2024, 20, 653–660。 doi:10.3762/bjoc.20.58