Herng, Tun Seng
Gopalakrishna, Tullimilli Y.
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AbstractThe 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.
CitationZeng W, Sun Z, Herng TS, Gonçalves TP, Gopalakrishna TY, et al. (2016) Super-heptazethrene. Angewandte Chemie International Edition 55: 8615–8619. Available: http://dx.doi.org/10.1002/anie.201602997.
SponsorsThis work was supported by the MOE Tier 3 programme (MOE2014-T3-1-004) and by an A*STAR JCO grant (1431AFG100). We thank Dr. Hiroyasu Sato in Rigaku Co. and Dr. Bruno Donnadieu in NUS for the crystallographic analysis.