Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes
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Author(s)
Dengiz, Cagatay
Luppino, Sarah
Gutierrez, Gregory D.
Swager, Timothy M
Date Issued
July 2017
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Dengiz, Cagatay, et al. “Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes.” The Journal of Organic Chemistry 82, 14 (July 2017): 7470–7480 © 2017 American Chemical Society
Version
Author's final manuscript
Abstract
The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels–Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF₂, as observed by ¹H NMR analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels–Alder adduct 10 is additionally demonstrated and enables us to direct its subsequent reactivity. Finally, this work serves to demonstrate the potential for naphthazarin as a building block in the synthesis of novel organic electronic materials.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/acs.joc.7b01170
