Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes

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2017-07-21

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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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Citation Formats

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.