Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes


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Dengiz C., LUPPINO S. P. , GUTIERREZ G. D. , SWAGER T. M.

JOURNAL OF ORGANIC CHEMISTRY, vol.82, no.14, pp.7470-7480, 2017 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 82 Issue: 14
  • Publication Date: 2017
  • Doi Number: 10.1021/acs.joc.7b01170
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.7470-7480

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 (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.