Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 18, Pages 5012-5016Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700441
Keywords
dyes/pigments; diradicaloids; near-infrared dyes; polycyclic aromatic hydrocarbons; quinones
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Funding
- MOE [MOE2014-T3-1-004, MOE2014-T2-1-080]
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Superbenzoquinone (SBQ) is a quinone derived from a classic polycyclic aromatic hydrocarbon (PAH), hexaperi-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.
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