Cu(OAc)₂‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes^†

Abstract

Comprehensive SummaryA series of unreported fullerodihydropyridine‐3‐ones were synthesized as a new family of fullerene derivatives in moderate to good yields by a simple one‐step reaction of [60]fullerene with cheap and readily available β‐substituted ethylamines in the absence or presence of arylacetaldehydes under the assistance of Cu(OAc)2. The in situ generation of arylacetaldehydes by the C—N bond cleavage of arylethylamines avoided their complex synthesis in advance and realized the preparation of fullerodihydropyridine‐3‐ones with structural and functional diversities, which may have promising applications in perovskite solar cells to improve the performance of photovoltaic devices due to the existence of a large π‐conjugated system on the dihydropyridine‐3‐one ring.

Selective deletion of one carbon atom from C60 through benzylamine mediated reactions

“…In addition, there are also evident interactions between the phenyl and the fullerene π systems. The shortest double bond on the fullerene cage is the isolated double CvC bond next to the imino group at 1.347 (3) Å. The four single C-C bonds around the two OH groups on the rim of the orifice are among the longest single bonds on the cage skeleton at around 1.55 Å.…”

“…1 Later, various isomerically pure amino fullerene derivatives were reported under various conditions. 2,3 Just like many other types of fullerene derivatives, the amino fullerenes were formed by addition reaction to the fullerene π-bonds. Amines have also been used to react with fullerene derivatives for further functionalization.…”