Diamino and Tetraamino Derivatives of Buckminsterfullerene C₆₀

Reactions between aliphatic amines and [60]fullerene: a review

“…corrected for total quantity of [60]fullerene consumed). The bisadducts thus formed have been carefully isolated and characterized [9,10]. Butts and Jazdzyk later demonstrated the photocycloaddition of substituted piperazines in good yield [11].…”

“…While the complex product mixtures generated upon reacting [60]fullerene with excess primary or secondary aliphatic amine are problematic to characterize, Kampe et al reported a simple method [9] for the generation of well-defined amine addition products using secondary diamines like N,N′-dimethylethylenediamine or piperazine (Fig. 2).…”

“…While the chemistry between [60]fullerene and aliphatic amines has been studied steadily over the past 15 years, there has been less attention paid to the reactions with polyamines [27], save the diamine chemistry [9][10][11] discussed above and a highly interesting reaction observed by Isobe et al upon mixing [60]fullerene and excess N,N′-dimethyl-1,3-diaminopropane in visible light and air saturated chlorobenzene [28]. A remarkable bis[60]fullerene adduct forms (Fig.…”

Electrochemical properties of two-component polymers of palladium and pyrrolidine and piperazine derivatives of C60

“…C 60 -piperazine mono-and bisadducts, pip-C 60 and (pip) 2 -C 60 , were synthesized according to previously described procedures [58][59][60]. (CH 3 )-pyr-C 60 and [(CH 3 ) 2 -pyr-C 60 ]I were synthesized using the straightforward "Prato Reaction" method [61,62] followed by the addition of methyliodide in a solution of toluene (Sigma Chemical Co.) to produce [(CH 3 ) 2 -pyr-C 60 ]I.…”

Hydrogenation of [60]fullerene with lithium in aliphatic amines

“…Simultaneously, because of the sensitivity of C 60 H 36 to light and oxygen [8], small satellite peaks (C 60 H 36 O þ , m=z ¼ 771:5) were observed. The electron deficiency of C 60 and nucleophilicity of aliphatic amines resulted in the formation of a trace of amine adducts [13] (C 60 H 35 (HNCH 2 -CH 2 NH) þ , m=z ¼ 813:6). Attempt to purify the hydrogenated product using TLC following other procedures [2] was frustrated because the R f value is zero.…”