Structural and electrochemical characterization of the products of the C₆₀–piperazine reaction

Abstract

Crystal structures of C60N2(C2H4)2 and C60{&(C2H4)2)2 show that addition occurs with elongation of the C-C bond at the 6: 6 ring junction to which the two nitrogen atoms are bonded; electrochemical one-electron reduction potentials of these adducts are shifted by ca. 0.1 V to more negative values for each added group.

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 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

“…For C 60 and C 70 , up to six one-electron steps have been observed in solution [22]. Additionally, a one-electron oxidation has also been observed for these fullerenes at relatively positive potentials [23].…”

“…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.…”

“…The formation, structure, and properties of C 60 /Pd films have been studied the most extensively [35][36][37][38], although, related films containing platinum, rhodium, and iridium have been also prepared [34,39]. Polymers of transition metals and fullerenes containing electron-donating groups, such as 2 -ferrocenylpyrrolidino- [3 ,4 ;1,2][C 60 ]fullerene and C 60 with covalently linked zinc meso-tetraphenylporphyrin, can be also synthesized under electrochemical conditions [40][41][42]. 0013 Conducting polymers can be reversibly oxidized and reduced leading to the switching between non-conducting and conducting states.…”