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Super‐heptazethrene
Author(s) -
Zeng Wangdong,
Sun Zhe,
Herng Tun Seng,
Gonçalves Théo P.,
Gopalakrishna Tullimilli Y.,
Huang KuoWei,
Ding Jun,
Wu Jishan
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602997
Subject(s) - diradical , intramolecular force , alkylation , dehydrogenation , derivative (finance) , molecule , open shell , singlet state , chemistry , ground state , computational chemistry , combinatorial chemistry , photochemistry , organic chemistry , catalysis , physics , atomic physics , financial economics , economics , excited state
The challenging synthesis of a laterally extended heptazethrene molecule, the super‐heptazethrene derivative SHZ‐CF3 , is reported. This molecule was prepared using a strategy involving a multiple selective intramolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. Compound SHZ‐CF3 exhibits an open‐shell singlet diradical ground state with a much larger diradical character compared with the heptazethrene derivatives. An intermediate dibenzo‐terrylene SHZ‐2H was also obtained during the synthesis. This study provides a new synthetic method to access large‐size quinoidal polycyclic hydrocarbons with unique physical properties.