Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes


Creative Commons License

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

JOURNAL OF ORGANIC CHEMISTRY, cilt.82, ss.7470-7480, 2017 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 82 Konu: 14
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1021/acs.joc.7b01170
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Sayfa Sayıları: ss.7470-7480

Özet

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.