Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes
JOURNAL OF ORGANIC CHEMISTRY, cilt.82, sa.14, ss.7470-7480, 2017 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 82 Sayı: 14
- Basım Tarihi: 2017
- Doi Numarası: 10.1021/acs.joc.7b01170
- Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.7470-7480
- Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
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.