10.1021/ja803593j
The study focuses on the electron transport and electrochemistry of fullerene derivatives with long-range ordered lamellar mesophases. The researchers synthesized fulleropyrrolidines with multi(alkyloxy)phenyl groups to achieve high carrier mobility in C60-containing mesomorphic materials, characterized by a high C60 content, compact packing, and highly ordered mesophase. The thermal properties of these derivatives were examined using differential scanning calorimetry (DSC), polarized optical microscopy (POM), and X-ray diffraction (XRD), revealing a long-range ordered lamellar mesophase similar to an ordered smectic phase. The study also explored the electrochemical activity of these materials, demonstrating that they are redox-active and possess a relatively large charge carrier mobility of approximately 3 × 10^-3 cm^2 V^-1 s^-1. The findings suggest that these mesomorphic fullerenes could be useful for designing soft materials with electrochemical and optoelectronic functions, and the long-range ordered lamellae could serve as "soft template" materials for the synthesis of two-dimensional polymers or layered materials with conductive or optical properties.
10.1021/jo001100q
The research focuses on the synthesis and characterization of a novel dyad molecule based on C60 (buckminsterfullerene) and bis(4′-tert-butylbiphenyl-4-yl)aniline (BBA) donor. The purpose of this study was to investigate the intramolecular charge-transfer interactions between the C60 moiety and the electron donor, BBA, with the aim of contributing to the development of artificial photosynthetic systems. The researchers synthesized the dyad 2 through a 1,3-dipolar addition of diazo compounds to C60 and characterized it using cyclic voltammetry (CV) and UV-vis spectra. The results indicated clear evidence of intramolecular charge-transfer interactions, as shown by a positive shift in the reversible oxidation wave of 2 compared to BBA in CV measurements and a significant hyperchromic effect in the UV-vis spectra. Chemicals used in the process included C60, BBA, tosylhydrazone 1, NaOCH3, and o-dichlorobenzene (ODCB), among others. The conclusions drawn from the study were that the synthesized C60-BBA dyad exhibited obvious evidence of intramolecular charge-transfer interactions in the ground state, which could have implications for the development of novel molecular electronic devices.
10.1021/ja909279b
The research discusses the construction of one-dimensional (1D) tubular structures through the self-assembly of laterally grafted rod amphiphiles and their coassembly with an aromatic rod and hydrophilic branched chain (compound 3). The purpose of the study was to create water-soluble toroids with a hydrophobic cavity that could encapsulate guest molecules, specifically C60 fullerenes. The researchers found that increasing the volume fraction of hydrophilic chains induced the formation of highly curved nanostructures, leading to the creation of discrete rings with a uniform cross-sectional diameter. These rings, composed of a single layer of molecules, had a hydrophobic interior and a hydrophilic exterior. Upon the addition of C60, the researchers observed that the fluorescence intensity of the solution decreased, indicating effective encapsulation of C60 within the hydrophobic interior of the rings. This encapsulation triggered the stacking of the toroids into tubular structures, which could potentially broaden the application scope of fullerenes. The chemicals used in this process include laterally grafted amphiphilic molecules 1 and 2, and compound 3, which consists of an aromatic rod and a hydrophilic branched chain.
10.1021/ja00221a084
The research focuses on the investigation of the photophysical and chemical properties of carbon-metal cluster ions, specifically those involving metal atoms such as lanthanum (La), potassium (K), and cesium (Cs) combined with spheroidal carbon cages. The purpose of the study was to test the hypothesis that metal atoms could be trapped inside closed carbon cages, such as the icosahedral carbon structure known as C60 or buckminsterfullerene. The researchers used laser vaporization of a graphite disk impregnated with the metal salts to produce these clusters in a supersonic beam. The conclusions drawn from the study suggest that the metal atoms are indeed encapsulated within the carbon cages, as evidenced by the high photophysical stability of the clusters, particularly C60La+. The chemicals used in the process included metal salts (lanthanum chloride, potassium, and cesium salts) and graphite as the source of carbon.
10.1016/j.tet.2012.04.061
The research presents a novel synthetic method for creating linear, diastereomerically pure fullerene triads, which are compounds consisting of two fullerene cages linked by an organic spacer. The purpose of this study is to develop a versatile and efficient route for synthesizing these triads, which have potential applications in molecular electronics, artificial photosynthetic systems, and supramolecular chemistry. The key chemicals used include fullerene C60 and C70, N,N'-dicyclohexylcarbodiimide (DCC) for activation, and various dicarboxylic acids and fulleropyrrolidines as precursors. The method involves functionalizing fullerene cages via a Prato reaction to form pyrrolidine rings, followed by a DCC-activated amidation reaction to link the fullerene cages. The study concludes that the yield of the coupling reaction is maximized in o-dichlorobenzene at high concentrations of the reactant fullerene nucleophile, while more polar solvents or lower concentrations favor the formation of unwanted side-products. The resultant triads exhibit good solubility in common organic solvents, enabling detailed characterization by NMR, IR, UV-vis spectroscopy, and MALDI-TOF mass spectrometry. This method allows for the flexible introduction of different fullerene cages and spacers, providing a wide range of symmetric and asymmetric fullerene structures without forming diastereomeric mixtures.
10.1016/0040-4020(96)00287-6
The research aimed to investigate the reaction of 2-azidobenzothiazole and 1-azido-4-(3',5'-dimethyl-1'-pyrazolyl)tetrafluorobenzene with [60]fullerene, leading to the formation of imino[60]fullerenes. The study sought to determine whether the formation of azafulleroid ([5-6]-π bonding type) or aziridinefullerene ([6-6]-α bonding type) could be explained by the duality of azide decomposition mechanisms. Through the use of fast-atom bombardment mass spectrometry (FAB-MS) and 13C NMR spectroscopy, the researchers established the structures of three new imino[60]fullerenes: two monoadducts (5 and 7) and one bisadduct (8). The chemicals used in the process included [60]fullerene, 2-azidobenzothiazole, 1-azido-4-(3',5'-dimethylpyrazol-1'-yl)tetrafluorobenzene, toluene, chlorobenzene, and various solvents and reagents for synthesis and characterization, such as sodium nitrite, hydrochloric acid, and m-nitrobenzyl alcohol (NBA) used as a matrix in the mass spectrometry analysis. The conclusions drawn from the study were that the reaction pathways could indeed lead to the formation of both types of imino[60]fullerenes, and the structural assignments of the adducts were confirmed through the spectroscopic techniques employed.