π-Extended Open-[70]Fullerenes with a Fused Azaacene

Bilateral π-extension of an open-[60]fullerene in a helical manner

“…Apart from the pristine (5,5) end-cap with a poor reactivity, open-[60]fullerenes are expected to be promising seeds for the growth of molecular CNTs. 8 The unilateral π-extension of open-[60]fullerenes has been developed by Iwamatsu 9 and us, 10 independently, in which a fused quinoxaline was introduced to the geodesic π-conjugation (Fig. 1).…”

Reactions of Diaminonaphthalenes with a Cage‐Opened C60 Derivative

“…According to the reported procedure, 2 was synthesized by a reaction of 1 with 2,3-diaminonaphthalene in ODCB (o-dichlorobenzene) (Figure 2a). [16] With the use of 1,2-diaminonaphthalene under similar conditions, two isomers, 3 a and 3 b, were obtained as a mixture in 87 % isolated yield. The ratio of 3 a/3 b was determined to be 74/26 by 1 H NMR, indicating the favored formation of 3 a.…”

“…ure 1), such as A (fused pyrazine, 20-atom ring) and B (fused imidazole, 17-atom ring). [16] In this work, we report a novel type of annulation mode C (fused pyrimidine, 17-atom ring) by the use of 1,8-diaminonaphthalene whereas reactions with 1,2-and 2,3-diaminonaphthalenes give type-A products. We also present a unique rearranged product as well as electronic properties of the three π-extended C 60 derivatives.…”

Construction of a 21‐Membered‐Ring Orifice on [60]Fullerene

“…This open-[60]fullerene is a suitable host for generating a variety of supramolecular complexes X@A where X is CO, [7] CH 4 , [8] NH 3 , [9] HCHO, [10] HCN, [10] and Ar. [11] In 2016, Yeh and coworkers demonstrated that a 24-membered-ring orifice (B), prepared from A [10] by a reaction with alcohol, allows for linear molecules such as HCN and C 2 H 2 to be inserted into the [60]fullerene cavity. [4] A huge orifice is also useful for trapping a chemically labile species such as H 2 O 2 under mild conditions (C) as shown by Lu, Gan, and co-workers in 2018.…”