Bilateral π-extension of an open-[60]fullerene in a helical manner

The conventional π-elongation of open-[60]fullerenes could only give unilaterally π-extended derivatives. Herein, we report the further π-elongation at another site to achieve bilateral π-elongation via a consecutive nucleophilic addition of 4,5-dimethyl- o -phenylenediamine. The thus-formed π-exten...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-05, Vol.59 (43), p.656-6563
Main Authors: Hashikawa, Yoshifumi, Sadai, Shumpei, Murata, Yasujiro
Format: Article
Language:English
Subjects:
Crystallography
Elongation
Fullerenes
Phenylenediamine
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Summary:The conventional π-elongation of open-[60]fullerenes could only give unilaterally π-extended derivatives. Herein, we report the further π-elongation at another site to achieve bilateral π-elongation via a consecutive nucleophilic addition of 4,5-dimethyl- o -phenylenediamine. The thus-formed π-extended open-[60]fullerene bears two-fold diaza[ n ]helicene ( n = 5 and 6) motifs in its skeleton. The crystallographic analysis revealed the characteristic helicene-fullerene interactions with close contacts of 3.09 and 3.14 Å. Bilateral π-elongation of an open-[60]fullerene produces a π-extended (5,5) end-cap with two-fold embedded diaza[ n ]helicene motifs.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc00784g