Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes
JOURNAL OF ORGANIC CHEMISTRY, vol.82, no.14, pp.7470-7480, 2017 (SCI-Expanded, Scopus)
- 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 (SCI-EXPANDED), Scopus
- Page Numbers: pp.7470-7480
- Open Archive Collection: AVESIS Open Access Collection
- Middle East Technical University Affiliated: No
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.