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

Autor: Hacker AS; Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu., Pavano M; Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu., Wood JE 2nd; Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu., Hashimoto H; Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu., D'Ambrosio KM; Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu., Frederickson CK; Department of Chemistry, 1252 University of Oregon, Eugene, OR 97403, USA., Zafra JL; Department of Physical Chemistry, University of Málaga, Andalucia-Tech, Campus de Teatinos s/n, 29071 Málaga, Spain. casado@uma.es., Gómez-García CJ; Instituto de Ciencia Molecular, Dpto. Química Inorgánica, Universidad de Valencia, 46980 Paterna, Valencia, Spain., Postils V; IKERBASQUE - Basque Foundation for Science (DC) & Donostia, International Physics Center & Kimika Fakultatea, Euskal Herriko Unibertsitatea (VP), Paseo Manuel de Lardizabal, 4, 20018 Donostia-San Sebastián, Euskadi, Spain., Ringer McDonald A; Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu., Casanova D; IKERBASQUE - Basque Foundation for Science (DC) & Donostia, International Physics Center & Kimika Fakultatea, Euskal Herriko Unibertsitatea (VP), Paseo Manuel de Lardizabal, 4, 20018 Donostia-San Sebastián, Euskadi, Spain., Frantz DK; Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, CA 93407, USA. dfrantz@calpoly.edu., Casado J; Department of Physical Chemistry, University of Málaga, Andalucia-Tech, Campus de Teatinos s/n, 29071 Málaga, Spain. casado@uma.es.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2019 Dec 07; Vol. 55 (94), pp. 14186-14189. Date of Electronic Publication: 2019 Nov 08.
DOI: 10.1039/c9cc07474k
Abstrakt: 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, 1 H-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.
Databáze: MEDLINE