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Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes
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Date
2017-07-21
Author
Dengiz, Çağatay
GUTIERREZ, Gregory D.
SWAGER, Timothy M.
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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 (HNMR)-H-1 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.
Subject Keywords
Organic Chemistry
URI
https://hdl.handle.net/11511/34274
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/acs.joc.7b01170
Collections
Department of Chemistry, Article
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Ç. Dengiz, G. D. GUTIERREZ, and T. M. SWAGER, “Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes,”
JOURNAL OF ORGANIC CHEMISTRY
, pp. 7470–7480, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34274.