Sulfur-Containing Homo- and Methanofullerenes: Synthesis and Study of Tribological Properties

The data obtained by the authors in the field of carbon cluster chemistry, namely the catalytic cycloaddition of sulfur-containing diazo compounds to C60-fullerene under the action of complex Pd catalysts, are summarized. Cycloaddition reactions of diazoalkanes, diazoketones, and diazothioates with C60-fullerene, catalyzed by Pd(acac)2–PPh3–Et3Al, with the selective formation of new sulfur-containing methano-, homo-, and pyrazolinofullerenes, are promising as modern nanosized additives in oils for highly loaded mechanisms

Catalytic Cycloaddition of Diazo Compounds Based on Pharmacologically Significant and Natural Compounds to C₆₀-Fullerene <xref rid="fn1-chemproc-2154902" ref-type="fn">†</xref>

The data obtained by the authors in the field of carbon cluster chemistry, namely, the catalytic cycloaddition of diazo compounds of modern pharmacologically significant and natural compounds to C60-fullerene under the action of complex Pd–catalysts, are summarized. Cycloaddition reactions of diazoacetates, diazoamides, and diazoketones with C60-fullerene, catalyzed by Pd(acac)2–PPh3–Et3Al, with the selective formation of methano– and pyrazolinofullerenes, are new and promising classes of biologically active derivatives of C60-fullerenes

One-Pot Method for the Synthesis of 2,5-Unsubstituted Pyrrolidino[3′,4′:1,9]fullerenes

A new, efficient process has been developed for the preparation of 2,5-unsubstituted pyrrolidino­[3′,4′:1,9]­fullerenes by the Ti­(O-<i>i</i>-Pr)₄-promoted reaction of fullerene C₆₀ with 1,3,5-perhydrotriazines generated in situ upon the reaction of primary alkyl- and benzylamines with paraformaldehyde and EtMgBr

Inheritance of photochromic properties of nitro-substituted and halogenated spiropyrans containing the pyrrolidino[60]fullerene

The photophysical and isomerization properties of hybrid molecular compounds that consist of photochromic nitro-substituted and halogenated spiropyran derivatives bonded to the surface of the [60]fullerene cage through the pyrrolidine bridge were investigated using various functionals and basis sets of TD-DFT and semiempirical quantum-chemical approaches. The role of nπ* states formed by the lone pairs of substituents in changing of the electronic structure and photochromic properties of spiropyran derivatives was evaluated. The Sππ(spiropyran) → intermediate nπ* states → Sππ(merocyanine) channel for phototransformation of the hybrid compound containing a nitro-substituted spiropyran moiety was established and compared with similar systems of halogenated spiropyrans attached to the [60]fullerene bulk where photoinduced isomerization does not process due to high probability of internal conversion from the excited electronic state localized on the spiropyran fragment to the states of the pyrrolidino[60]fullerene

Fullerenyl-1,2,3-Triazoles: Synthesis and Cytotoxic Activity

Through the reaction of fullerenylazide with terminal acetylenes, previously undescribed 1-butyl-2-triazolylfullerenes, in which the heterocyclic fragment was directly attached to the fullerene backbone, were synthesized for the first time. Water-soluble complexes of the synthesized adducts of fullerene with polyvinylpyrrolidone showed a high cytotoxic activity towards tumor cells of the Jurkat, K562, and U937 lines

Synthesis and Properties of Energy-Rich Methanofullerenes Containing Norbornadiene and Quadricyclane Moieties

The energy-rich methanofullerenes were synthesized for the first time by the reaction of fullerene C₆₀ with mono- and bisquadricyclane esters of malonic acid. The C–C bond cleavage in the quadricyclane moieties of new hybrid molecules takes place in the presence of catalytic amounts of Cu, Pd, and Pt salts or complexes or SiO₂ and is accompanied by heat evolution

Aminomethylation of Fullerene C₆₀ with <i>N</i>,<i>N</i>′,<i>N</i>″‑Triaryl- or <i>N</i>,<i>N</i>′,<i>N</i>″‑Trihetaryl-1,3,5-perhydrotriazines in the Presence of EtMgBr and Ti(O<i>i</i>‑Pr)₄

A new method for the functionalization of fullerenes based on the reaction between in situ generated aryl- or hetaryl-containing 1,3,5-perhydrotriazines and EtMgBr in the presence of Ti­(O<i>i</i>-Pr)₄ has been developed. The cleavage of the triazine ring under previously developed conditions− results in the formation of aminomethylated derivatives of fullerene C₆₀ with high yields (80–90%) and selectivity (∼90%)

Inheritance of Photochromic Properties of Nitro-Substituted and Halogenated Spiropyrans Containing the Pyrrolidino[60]fullerene

The photophysical and isomerization properties of hybrid molecular compounds that consist of photochromic nitro-substituted and halogenated spiropyran derivatives bonded to the surface of the [60]­fullerene cage through the pyrrolidine bridge were investigated using various functionals and basis sets of TD-DFT and semiempirical quantum-chemical approaches. The role of <i>n</i>π* states formed by the lone pairs of substituents in changing of the electronic structure and photochromic properties of spiropyran derivatives was evaluated. The S_ππ(spiropyran) → intermediate <i>n</i>π* states → S_ππ(merocyanine) channel for phototransformation of the hybrid compound containing a nitro-substituted spiropyran moiety was established and compared with similar systems of halogenated spiropyrans attached to the [60]­fullerene bulk where photoinduced isomerization does not process due to high probability of internal conversion from the excited electronic state localized on the spiropyran fragment to the states of the pyrrolidino[60]­fullerene

Aminomethylation of Fullerene C₆₀ with <i>N</i>,<i>N</i>′,<i>N</i>″‑Triaryl- or <i>N</i>,<i>N</i>′,<i>N</i>″‑Trihetaryl-1,3,5-perhydrotriazines in the Presence of EtMgBr and Ti(O<i>i</i>‑Pr)₄

A new method for the functionalization of fullerenes based on the reaction between in situ generated aryl- or hetaryl-containing 1,3,5-perhydrotriazines and EtMgBr in the presence of Ti­(O<i>i</i>-Pr)₄ has been developed. The cleavage of the triazine ring under previously developed conditions− results in the formation of aminomethylated derivatives of fullerene C₆₀ with high yields (80–90%) and selectivity (∼90%)