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Org Lett. 2011 Jul 1;13(13):3316-9. doi: 10.1021/ol201004u. Epub 2011 Jun 7.

Open-shell singlet character of stable derivatives of nonacene, hexacene and teranthene.

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Key Laboratory for Biomedical Effects of Nanomaterials and Nanosafety, Institute of High Energy Physics, Chinese Academy of Sciences, Beijing, 100049, China.


The electronic ground states of the recently synthesized stable nonacene derivatives (J. Am. Chem. Soc. 2010, 132, 1261) are open-shell singlets with a polyradical nature instead of closed-shell singlets as originally assumed, according to the unrestricted broken spin-symmetry density functional theory (UBS-DFT) computations (at B3LYP/6-31G*). It is the bulky protecting groups, not the transfer from the open-shell singlet to closed-shell singlet ground state, that stabilizes these longest characterized acenes. Similar analyses also confirmed the open-shell singlet character of the hexacene and teranthene derivatives.

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