Abstract
Curved π-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved π surface. However, the synthesis of such distorted molecules requires harsh conditions, which hamper easy access to heteroatom-containing curved π systems. Here we report the synthesis of a π-extended azacorannulene with nitrogen in its centre. The oxidation of 9-aminophenanthrene provides tetrabenzocarbazole, which is converted to the azabuckybowl through palladium-catalysed intramolecular coupling. The electron-donating nature and curved π surface of the azabuckybowl enable its tight association with C60 in solution and solid states. High charge mobility is observed for the azabuckybowl/C60 assembly. This compound may be of interest in the fields of curved π systems as fullerene hosts, anisotropic π donors and precursors to nitrogen-containing nanocarbon materials.
Highlights
Curved p-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved p surface
Curving a p system induces a large displacement from a plane to construct threedimensional structures[5,6,7,8,9,10]
Consecutive fusion reactions of tetrabenzocarbazole 2 through palladium-catalysed C–H/C–Cl and C–H/C–Br coupling achieve the synthesis of nitrogenembedded buckybowl 5, that is, ‘azabuckybowl’[28] under mild conditions
Summary
Curved p-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved p surface. High charge mobility is observed for the azabuckybowl/C60 assembly This compound may be of interest in the fields of curved p systems as fullerene hosts, anisotropic p donors and precursors to nitrogen-containing nanocarbon materials. Curving a p system induces a large displacement from a plane to construct threedimensional structures[5,6,7,8,9,10] Besides their figurative beauty, the curved p surface generates unique functions such as chiroptical properties, anisotropic electron transitions and dynamic motion in solution and solid states[11,12,13]. The curved p surface generates unique functions such as chiroptical properties, anisotropic electron transitions and dynamic motion in solution and solid states[11,12,13] To enhance these characteristics, the introduction of heteroatoms is an effective strategy. Owing to the electron-donating nature of the nitrogen atom, azabuckybowl 5 strongly interacts with C60 to furnish an inclusion complex, which exhibits a substantially high chargecarrier mobility in the solid state
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