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Toward Stable Superbenzoquinone Diradicaloids
Author(s) -
Li Guangwu,
Phan Hoa,
Herng Tun Seng,
Gopalakrishna Tullimilli Y.,
Liu Chunchen,
Zeng Wangdong,
Ding Jun,
Wu Jishan
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700441
Subject(s) - diradical , chemistry , quinone , singlet state , reactivity (psychology) , combinatorial chemistry , stereochemistry , physics , excited state , medicine , alternative medicine , pathology , nuclear physics
Superbenzoquinone (SBQ) is a quinone derived from a classic polycyclic aromatic hydrocarbon (PAH), hexa‐ peri ‐hexabenzocoronene (so‐called “superbenzene”), and is a challenging synthetic target. Herein we report the successful synthesis and characterization of its derivatives. We reveal that the high reactivity of SBQ is due to its intrinsic open‐shell diradical character. Thus, two kinetically blocked SBQs, SBQ‐Me and SBQ‐Ph , were prepared by different synthetic strategies. 4‐ tert ‐Butylphenyl‐substituted SBQ‐Ph demonstrated good stability and could be isolated in crystalline form. Both compounds have an open‐shell singlet ground state and show thermally populated paramagnetic activity. Our studies provide effective strategies toward stable quinone‐based diradicaloids.