Artur A. Khuzin

Catalytic cycloaddition of diazoalkanes with heterocyclic substituents to fullerene C60

Methanofullerenes were directly synthesized under mild conditions by cycloaddition to fullerene C60 of diazoalkanes generated in situ by oxidation of ketone hydrazones containing a heterocyclic fragment with manganese(IV) oxide in the presence of the catalytic system Pd(acac)2-2 PPh3-4 Et3Al.

Synthesis, structure and photochromic properties of hybrid molecules based on fullerene C60 and spiropyrans

The 1,3-dipolar cycloaddition of azomethine ylides to fullerene C60 was utilized to perform the synthesis of spiropyran-containing photochromic pyrrolidinofullerenes. It was found that photochromism is observed only for the hybrid compound containing an NO2 group in the pyran moiety, whereas the pyrrolidinofullerenes with Cl or F atoms in the spiropyran moiety do not possess photochromism. The photochromic fullerene hybrid is characterized by lower light sensitivity and photodegradation parameters compared to the initial spiropyrans, which can be attributed to reabsorption of activating radiation.

Light-controlled molecular switches based on carbon clusters. Synthesis, properties and application prospects

The review integrates and analyzes the experimental and theoretical studies published in the last 15 years dealing with the synthesis and physicochemical and photochromic properties of the hybrid molecules based on carbon clusters (fullerenes, nanotubes and graphene) and photochromic molecules (diarylethenes, spiropyrans, spirooxazines and azobenzene). The state-of-the-art trends of the application of photochromic compounds as light-controlled electronic devices, sensors and optical memory elements are considered. The main types of optical molecular switches derived from carbon clusters are described. The synthetic approaches to these hybrid molecules and the relationships between their structure and photochromic properties are discussed.The bibliography includes 199 references.

Synthesis and Tribological Properties of Sulfur-Containing Methanofullerenes

Functionally substituted sulfur-containing methanofullerenes have been synthesized by cycloaddition of diazothiotates and C60 fullerene in the presence of the three-component catalyst Pd(acac)2–2PPh3–4Et3Al. The sulfur-containing fullerenes as nanomodifiers for additives (0,005wt%) improve antiwear and EP (extreme pressure) characteristics of industrial oil I-20А.

Aminomethylation of Fullerene C60 with N,N′,N″-Triaryl- or N,N′,N″-Trihetaryl-1,3,5-perhydrotriazines in the Presence of EtMgBr and Ti(Oi-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(Oi-Pr)4 has been developed. The cleavage of the triazine ring under previously developed conditions1-6 results in the formation of aminomethylated derivatives of fullerene C60 with high yields (80-90%) and selectivity (∼90%).

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.

Synthesis and photochromic properties of hybrid molecules based on fullerene C 60 and 3,3′-(cyclopent-1-ene-1,2-diyl)bis(5-chloro-2-methylthiophene)

A series of C60 adducts with azides derived from 3,3′-(cyclopent-1-ene-1,2-diyl)bis(5-chloro-2-methylthiophene) have been synthesized for the first time, and their photochromic properties have been studied. The effects of the structure of the spacer connecting the fullerene and dihetarylethene moieties and electronic structure of the fullerene skeleton on the efficiency of photoinduced transformations of the new hybrid molecules have been estimated.