Synthesis of N-acylated fulleropyrrolidines: New materials for the preparation of Langmuir-Blodgett films containing fullerenes

Lanthanum Endohedral Metallofulleropyrrolidines: Synthesis, Isolation, and EPR Characterization

“…[13,14] The fulleropyrrolidines thus formed present novel properties that are absent for the pristine C 60 . [15,16] Addition of azomethine ylides to C 60 and carbon nanotubes has generated some applicable materials such as C 60 -modified HPLC stationary phases, [17] C 60 -functionalized unnatural peptides with antimicrobial activity against two representative bacteria, [18] and soluble carbon nanotubes suitable for preparation of nanocomposites. [19,20] Yet to the best of our knowledge, the Prato reaction has never been exploited for functionalization of metallofullerenes; endohedral fulleropyrrolidines have not been reported yet.…”

Cycloadditions

“…Further side-chain chemistry can be carried out either at one of the side chains attached to the five-membered ring [228][229][230][231][232] or at the pyrrolidine nitrogen [215,224,231,[233][234][235][236][237][238][239]. For example, upon heating 3-triphenylmethyloxazolidin-5-one (210) at reflux for 16 h with C 60 in equimolar amounts, 211 can be isolated in 39% yield [204].…”

“…Amine 212 was also coupled with peptides [233], acetic anhydride [215,234], dinitrobenzoyl chloride [235] or a ferrocene carboxylic acid chloride [215,236] in good yields. Reaction with dinitrochlorobenzene [237] or dinitrofluorobenzene [238] proceeds via nucleophilic aromatic substitution in the presence of K 2 CO 3 or NaH.…”

N‐Unsubstituted and N‐Arylated Fulleropyrrolidines: New Useful Building Blocks for C60 Functionalization†

“…[4][5][6] Introduction of additional functional groups at the N-1 or C-2 position can be realized by further modification of the pyrrolidine moiety or incorporating specific functional groups to the precursors of the addition reaction. For the N-1 position-based approach, a flexible aliphatic linker is usually used to anchor a functional group to the nitrogen atom (1a), [7][8][9][10][11] while the second approach always leads to dissymmetric structures due to the tetravalency of the C-2 atom (1b). 12 We recently reported a new series of hydrogen bonding-driven foldamer-based porphyrin tweezers, which can efficiently complex C 60 , C 70 and their deriva-tives.…”