A heterocycle-to-heterocycle strategy is presented for the preparation of highly fluorescent and solvatochromic dibenzonaphthyridinones (DBNs) via methodology that leads to the formation of a tertiary, spiro-fused carbon center. A linear correlation between the results of photophysical experiments and time dependent density functional theory calculations was observed for the λmax of excitation for DBNs with varying electronic character.
Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies and Photophysical Studies. -The two-step preparation of dibenzonaphthyridinones via 3,5-bis(2-nitrophenyl)-1,2-oxazoles is described. The photochemical properties of the products are examined experimentally and computationally. -(PALAZZO, T. A.; PATRA, D.; YANG, J. S.; EL KHOURY, E.; APPLETON, M. G.; HADDADIN, M. J.; TANTILLO, D. J.; KURTH*, M. J.; Org. Lett. 17 (2015) 23, 5732-5735, http://dx.doi.org/10.1021/acs.orglett.5b02680 ; Dep. Chem., Univ. Calif., Davis, CA 95616, USA; Eng.) -F. Schill 16-163
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