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Fluoreno[2,1-a]fluorene: an ortho-naphthoquinodimethane-based system with partial diradical character

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Abstract

Fluoreno[2,1-a]fluorene, a molecule comprising fused ortho-quinodimethane units in a 1,5-napthoquinodimethane core, has been prepared and investigated with spectroscopy (UV-Vis-NIR, 1H-NMR and Raman), SQUID magnetometry, spectroelectrochemistry and quantum chemistry. While para-quinodimethanes with a 2,6-substitution pattern exist as closed-shell species and meta-quinodimethanes with 2,7-substitution favour a ground electronic state with very large diradical character, our 1,5-substituted ortho-naphthoquinodimethane-based system exhibits an intermediate degree of diradical character.

Graphical abstract: Fluoreno[2,1-a]fluorene: an ortho-naphthoquinodimethane-based system with partial diradical character

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Publication details

The article was received on 24 Sep 2019, accepted on 25 Oct 2019 and first published on 25 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC07474K
Chem. Commun., 2019, Advance Article

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    Fluoreno[2,1-a]fluorene: an ortho-naphthoquinodimethane-based system with partial diradical character

    A. S. Hacker, M. Pavano, J. E. Wood, H. Hashimoto, K. M. D’Ambrosio, C. K. Frederickson, J. L. Zafra, C. J. Gómez-García, V. Postils, A. Ringer McDonald, D. Casanova, D. K. Frantz and J. Casado, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC07474K

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