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Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes

Author(s)
Dengiz, Cagatay; Luppino, Sarah; Gutierrez, Gregory D.; Swager, Timothy M
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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.
Date issued
2017-07
URI
http://hdl.handle.net/1721.1/116849
Department
Massachusetts Institute of Technology. Department of Chemistry
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
ISSN
0022-3263
1520-6904

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