Synthesis of Acenaphthene Fused Dithiaporphyrin(3.1.1.1)s and N-Fused Triphyrin(3.1.1)s in One-Pot Condensation

Two different types of novel nonaromatic acenaphthene fused macrocycles such as acenaphthene fused dithiaporphyrin(3.1.1.1)s and acenaphthene fused N-fused triphyrin(3.1.1)s were synthesized in one pot condensation reaction using 5,6-dibromoacenaphthene as a key precursor. The X-ray analysis revealed the oval core-shaped structure for dithiaporphyrin(3.1.1.1)s and intramolecular ring fusion in N-Fused triphyrin(3.1.1)s. The NMR, absorption and DFT studies suggested the non-aromatic nature of both macrocycles which absorb strongly in visible-NIR region. Both macrocycles were stable under electrochemical conditions and showed their electron-rich nature.