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Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes

Yixun Sun, Xin Wang, Bo Yang, Muhua Chen, Ziyi Guo, Yiting Wang, Ji Li, Mingyu Xu, Yunjie Zhang, Huaming Sun, Jingshuang Dang, Juan Fan, Jing Li () and Junfa Wei ()
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Yixun Sun: Shaanxi Normal University
Xin Wang: Shaanxi Normal University
Bo Yang: Shaanxi Normal University
Muhua Chen: Shaanxi Normal University
Ziyi Guo: Shaanxi Normal University
Yiting Wang: Shaanxi Normal University
Ji Li: Shaanxi Normal University
Mingyu Xu: Shaanxi Normal University
Yunjie Zhang: Shaanxi Normal University
Huaming Sun: Shaanxi Normal University
Jingshuang Dang: Shaanxi Normal University
Juan Fan: Shaanxi Normal University
Jing Li: Shaanxi Normal University
Junfa Wei: Shaanxi Normal University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract 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 C60 or C70, which are driven by concave-convex π ⋯ π interactions and multiple C–H ⋯ π interactions between bowl and fullerenes.

Date: 2023
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DOI: 10.1038/s41467-023-39086-0

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