Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes

• Published in: Nature communications 2023-06, Vol.14 (1), p.3446-3446, Article 3446
• Main Authors: Sun, Yixun, Wang, Xin, Yang, Bo, Chen, Muhua, Guo, Ziyi, Wang, Yiting, Li, Ji, Xu, Mingyu, Zhang, Yunjie, Sun, Huaming, Dang, Jingshuang, Fan, Juan, Li, Jing, Wei, Junfa
• Format: Article
• Language: English
• Subjects: 639/301/923/3931; 639/638/403/933; 639/638/403/936; Aldehydes; Aromatic compounds; Carbon; Chlorine; Crystallography; Crystallography, X-Ray; Fullerenes; Fullerenes - chemistry; Humanities and Social Sciences; Methylene; multidisciplinary; Science; Science (multidisciplinary); Selenium; Structural strain; Sulfur; Supramolecular compounds; Synthesis; X-ray crystallography
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-023-39086-0

Synthesis of buckybowls have stayed highly challenging due to the large structural strain caused by curved π surface. In this paper, we report the synthesis and properties of two trichalcogenasupersumanenes which three chalcogen (sulfur or selenium) atoms and three methylene groups bridge at the bay regions of hexa- peri -hexabenzocoronene. These trichalcogenasupersumanenes are synthesized quickly in three steps using an Aldol cyclotrimerization, a Scholl oxidative cyclization, and a Stille type reaction. X-ray crystallography analysis reveals that they encompass bowl diameters of 11.06 Å and 11.35 Å and bowl depths of 2.29 Å and 2.16 Å for the trithiasupersumanene and triselenosupersumanene, respectively. Furthermore, trithiasupersumanene derivative with methyl chains can form host-guest complexes with C 60 or C 70 , which are driven by concave-convex π  ⋯  π interactions and multiple C–H ⋯  π interactions between bowl and fullerenes. Synthesis of buckybowls has remained challenging due to the inherent high strain induced by the curvature. Herein, the authors report the synthesis of two bowl-shaped polycyclic aromatics with three chalcogen atoms and three methylene groups embedded at the bay regions of hexa- peri -hexabenzocoronene and demonstrate guest host complexation with trithiasupersumanene.