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J Org Chem. 2018 Jan 19;83(2):690-702. doi: 10.1021/acs.joc.7b02674. Epub 2017 Dec 29.

Dibenzopyrrolo[1,2-a][1,8]naphthyridines: Synthesis and Structural Modification of Fluorescent L-Shaped Heteroarenes.

Author information

1
Department of Chemistry, Faculty of Science, Tokyo University of Science , Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
2
Department of Chemistry, Graduate School of Science, University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
3
International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba , 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan.
4
Course of Chemical Engineering, National Institute of Technology , Anan Collage, 265 Aoki, Minobayashi, Tokushima 774-0017, Japan.

Abstract

The L-shaped, π-extended pentacycle dibenzopyrrolo[1,2-a][1,8]naphthyridine and its derivatives were synthesized using two methods: fully intramolecular [2 + 2 + 2] cycloaddition and oxidative aromatization using substituted carbodiimide and modification of an electron-rich indole ring of an L-shaped skeleton via electrophilic reaction and cross-coupling. These L-shaped compounds emitted fluorescence in high quantum yield. The position of substituents affected the fluorescence color through two different mechanisms, π-conjugation and skeletal distortion, which caused the substituted L-shaped compounds to emit fluorescence in a variety of colors and to exhibit solvato-fluorochromism.

PMID:
29231717
DOI:
10.1021/acs.joc.7b02674

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