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Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes.

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.

SUBMITTER: Sun Y

PROVIDER: S-EPMC10257710 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes.

Sun Yixun Y Wang Xin X Yang Bo B Chen Muhua M Guo Ziyi Z Wang Yiting Y Li Ji J Xu Mingyu M Zhang Yunjie Y Sun Huaming H Dang Jingshuang J Fan Juan J Li Jing J Wei Junfa J

Nature communications 20230610 1

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 r ...[more]

PMID: 37301852

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Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes.

Publications

Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes.

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