Synlett 2023; 34(04): 374-378
DOI: 10.1055/a-1992-0487
letter

Pentagon-Fused Sumanenes on the Aromatic Peripheries en Route to the Bottom-Up Synthesis of Fullerenes

Hironobu Nakazawa
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
,
Yuta Uetake
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
,
Yumi Yakiyama
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
,
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
› Author Affiliations
This work was supported by JSPS KAKENHI, grant nos. JP26102002, JP21H05233, JP19H00912, JP20H00400 (H.S.), and JP20K15279 (Y.U.). and Grant-in-Aid for JSPS Research Fellow JP21J10937 (H.N.).


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Abstract

Bowl-shaped π-conjugated sumanenyltriamines were successfully synthesized in a one-step reaction from bromomethylsumanene. This molecule represents an example of hemiazafullerene (C54N6 fragment) with six isolated pentagons. Its single-crystal X-ray structural analysis showed the formation of one-dimensional columnar structures incorporating chloroform. The hemifullerene (C30 fragment) was also synthesized when the nucleophile was changed to dimethylmalonate.



Publication History

Received: 20 November 2022

Accepted after revision: 02 December 2022

Accepted Manuscript online:
02 December 2022

Article published online:
03 January 2023

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