Journal
CHEMICAL COMMUNICATIONS
Volume 55, Issue 62, Pages 9100-9103Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc04564c
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Funding
- MOE Tier 3 programme [MOE2014-T3-1-004]
- NRF Investigatorship [NRF2018NRF-NRFI001-05]
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We report the synthesis and electronic properties of nitrogen-doped heptazethrene (HZ) and octazethrene (OZ) diradicaloids, including the parent HZ-1N and OZ-1N, and the N-aryl-substituted dications, HZ-2N and OZ-2N. The unprotected HZ-1N and OZ-1N were generated in situ, but they are not stable enough for isolation. On the other hand, the N-aryl precursors 7a/7b were prepared by using a one-pot Buchwald-Hartwig amination followed by the intramolecular cyclization strategy. Chemical oxidation of 7a/7b gave the corresponding dications, HZ-2N/OZ-2N. HZ-2N displayed an open-shell singlet ground state with a moderate diradical character (y(0) = 27.2%) and a small singlet-triplet energy gap (Delta ES-T = -4.9 kcal mol(-1)). OZ-2N with larger diradical character (y(0) = 54.7%) is more reactive and underwent the hydrogen abstraction reaction.
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