Synthesis of a green [60]fullerene derivative through cage-opening reactions

Abstract

Open-cage derivative C(60)(O)(4)(OH)(2)(NC(6)H(4)(t)Bu)(2) reacts with ICl to form a Baeyer-Villiger type product, which yields an intense green product upon treatment with HI.

A green fullerene derivative as a fluoride ion sensor

“…Compound 3 has been reported before in two steps from 2. 15 It has an imino anhydride moiety instead of the imide moiety in 1. Both compounds 3 and 1 are very stable and their interconversion was not achieved (Scheme 3).…”

Peroxide‐Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open‐Cage Fulleroid C55O5

“…Functional groups on the rim of the orifice can be used to fine‐tune the electronic structure of the π system and to connect to other chromophores. The green open‐cage fullerene derivative 38 was prepared from 32 in two steps (Scheme ) . It shows intense absorption in the 600–800 nm range.…”

Open‐cage fullerenes as tailor‐made container for a single water molecule

“…Most of the reactions take place around one central pentagon on the C 60 cage. Several routes have been developed to cleave three adjacent double bonds around the same pentagon to form open‐cage fullerenes with orifices large enough for water encapsulation …”

“…Starting from the transformation of the epoxide moiety of 14 , open‐cage compound 15 was obtained in 8 steps with 5.8% overall yield (for Ar = Ph) . The remaining peroxo group in 15 can be further reduced to a hydroxyl group to form the C s symmetric 16 , which can be converted to 17 and 18 upon treatment with ICl/H 2 O and TsOH, respectively . The orifice sizes of compounds 15 , 16 , 17 and 18 are similar to that of compound 12 .…”