The replacement of a ketone with a sulfide moiety changes the electronic properties of cage-opened fullerene ylides, thus causing a hypsochromic shift in absorption and a cathodic shift of reduction potentials.
Fullerene–graphene
hybrids potentially exhibit unprecedented
properties owing to interactive communication between the two units
through a linkage. However, most of their discrete molecular structures
have been still undisclosed thus far. With the recent rise in the
awareness of facile access to molecular nanocarbon hybrids, we showcase
novel π-extended fullerenes with a fused pyrazine or imidazole.
Owing to the effective planar–curved π-conjugation, their
absorption coefficients significantly increased in the visible region.
Curiously enough, during the formation of π-extended fullerenes,
an in situ generated NH3 molecule was spontaneously encapsulated
inside the fullerene cavity. The NH3 molecule then underwent
a timed orifice-expansion triggered by its sustained release. This
is the first demonstration that fullerene captures a reactant inside,
suggesting their potential usage for a sustained dosing and/or material
delivery toward postfunctionalization of fullerene–graphene
hybrids.
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