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Fluoreno[2,1-a]fluorene: an ortho-naphthoquinodimethane-based system with partial diradical character
Allison S Hacker1, Mauricio Pavano1, James E Wood1
1Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu.
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.
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