In 1972, Baird showed theoretically that the electron counting rule for aromaticity and antiaromaticity in the lowest ππ* triplet state is opposite to that in the electronic ground state. A pair of compounds that manifests this reversal in character has now been identified and characterized experimentally for the first time.
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References
Hückel, E. Z. Physik 70, 204–286 (1931).
Heilbronner, E. Tetrahedron Lett. 5, 1923–1928 (1964).
Ajami, D., Oeckler, O., Simon, A. & Herges, R. Nature 426, 819–821 (2003).
Baird, N. C. J. Am. Chem. Soc. 94, 4941–4948 (1972).
Gogonea, V., Schleyer, P. v. R. & Schreiner, P. R. Angew. Chem. Int. Ed. 37, 1945–1948 (1998).
Rosenberg, M., Dahlstrand, C., Kilså, K. & Ottosson, H. Chem. Rev. 114, 5379–5425 (2014).
Sung, Y. M. et al. Nature Chem. 7, 418–422 (2015).
Yoon, Z. S. et al. J. Am. Chem. Soc. 128, 14128–14134 (2006).
Sankar, J. et al. J. Am. Chem. Soc. 130, 13568–13579 (2008).
Mori, S. & Osuka, A. J. Am. Chem. Soc. 127, 8030–8031 (2005).
Rath, H. et al. Chem. Commun. 3762–3764 (2009).
Zilberg, S. & Haas, Y. J. Phys. Chem. A 102, 10851–10859 (1998).
Karadakov, P. J. Phys. Chem. A 112, 7303–7309 (2008).
Karadakov, P. J. Phys. Chem. A 112, 12707–12713 (2008).
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Ottosson, H., Borbas, K. A light-switched yin and yang pair. Nature Chem 7, 373–375 (2015). https://doi.org/10.1038/nchem.2242
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DOI: https://doi.org/10.1038/nchem.2242