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assemblies and nanofunctional materials in the field of optoelectronic devices, catalysis, biomedicines, and so on. [4] On one hand, C 60 has a triple degenerate lowest unoccupied molecule orbital (LUMO), presenting a good electron-accepting ability for holding up to six electrons and facilitating the formation of donor-acceptor dyads. On the other hand, it can be viewed as electron-deficient polyalkene and, therefore, chemically reactive. [5] These two features make the derivatization of fullerene feasible so as to extend its functionality. Various kinds of molecules/ structures have been linked to fullerenes to form fullerenes derivatives. For example, biphenyl fulleroids (Ph 2 C 61) was first synthesized by Suzuki et al. in 1991, [6] which was followed soon by the synthesis of Phenyl-C61-butyric acid methyl ester (PC 61 BM). [7] The latter was demonstrated advantageous in organic photovoltaics (OPVs) by enhancing the open-circuit voltage. [8] Meanwhile, physical and chemical modifications of fullerene have been achieved by linking to other molecular structures. By combining the distinctive features of fullerenes and unique physical properties of the linked molecules, advanced fullerene derivative materials with novel physicochemical characteristics can be synthesized. Some of these fullerene derivative materials have been demonstrated to possess great electrical, [9] thermal, [10] optical, [11] photovoltaic, [12] and solubility properties, [12] which could be applied in photovoltaic, [13] optical, [10c] and temperature sensors. [14] The cage-shaped space of fullerene derivatives can be used to trap small molecules. These small molecules, in turn, modify the electronic properties of the fullerene derivatives, leading to various structures of the fullerene derivatives with peculiar and exceptional phenomenon. The design and development of such molecular containers with a discrete structure for the uptake of small molecules represent attractive research targets. Recently, the synthesis of open-cage fullerene with a circular 17-membered-ring opening, which contains one sulfur atom on the rim, was reported. [15] Murata and co-workers trapped N 2 and CO 2 molecules in the confined internal sub-nano spaces of the open-cage fullerene derivatives. Subsequently, by encapsulating a NO molecule into an open-cage fullerene derivative, a metal-free electron spin system was successfully constructed. [16] The synthetic methods to insert small molecules into fullerene derivatives have been extensively studied. [17] Very recently, Han et. al., synthesized a variety of hollow C 60 nanostructures, using the xylene template, with tailored shapes, such as two-node calabash. [18] This methodology not only expands the synthetic Hollow nanostructures are widely used in chemistry, materials, and bioscience due to their excellent electrochemical and photoelectric properties. Recently, hollow fullerene nanostructures with tailored opening and shapes have been synthesized. Here, the transport properties of two-node hollow-fullerene-based ...
assemblies and nanofunctional materials in the field of optoelectronic devices, catalysis, biomedicines, and so on. [4] On one hand, C 60 has a triple degenerate lowest unoccupied molecule orbital (LUMO), presenting a good electron-accepting ability for holding up to six electrons and facilitating the formation of donor-acceptor dyads. On the other hand, it can be viewed as electron-deficient polyalkene and, therefore, chemically reactive. [5] These two features make the derivatization of fullerene feasible so as to extend its functionality. Various kinds of molecules/ structures have been linked to fullerenes to form fullerenes derivatives. For example, biphenyl fulleroids (Ph 2 C 61) was first synthesized by Suzuki et al. in 1991, [6] which was followed soon by the synthesis of Phenyl-C61-butyric acid methyl ester (PC 61 BM). [7] The latter was demonstrated advantageous in organic photovoltaics (OPVs) by enhancing the open-circuit voltage. [8] Meanwhile, physical and chemical modifications of fullerene have been achieved by linking to other molecular structures. By combining the distinctive features of fullerenes and unique physical properties of the linked molecules, advanced fullerene derivative materials with novel physicochemical characteristics can be synthesized. Some of these fullerene derivative materials have been demonstrated to possess great electrical, [9] thermal, [10] optical, [11] photovoltaic, [12] and solubility properties, [12] which could be applied in photovoltaic, [13] optical, [10c] and temperature sensors. [14] The cage-shaped space of fullerene derivatives can be used to trap small molecules. These small molecules, in turn, modify the electronic properties of the fullerene derivatives, leading to various structures of the fullerene derivatives with peculiar and exceptional phenomenon. The design and development of such molecular containers with a discrete structure for the uptake of small molecules represent attractive research targets. Recently, the synthesis of open-cage fullerene with a circular 17-membered-ring opening, which contains one sulfur atom on the rim, was reported. [15] Murata and co-workers trapped N 2 and CO 2 molecules in the confined internal sub-nano spaces of the open-cage fullerene derivatives. Subsequently, by encapsulating a NO molecule into an open-cage fullerene derivative, a metal-free electron spin system was successfully constructed. [16] The synthetic methods to insert small molecules into fullerene derivatives have been extensively studied. [17] Very recently, Han et. al., synthesized a variety of hollow C 60 nanostructures, using the xylene template, with tailored shapes, such as two-node calabash. [18] This methodology not only expands the synthetic Hollow nanostructures are widely used in chemistry, materials, and bioscience due to their excellent electrochemical and photoelectric properties. Recently, hollow fullerene nanostructures with tailored opening and shapes have been synthesized. Here, the transport properties of two-node hollow-fullerene-based ...
The endohedral fullerene CH 4 @C 60 ,i nw hich each C 60 fullerene cage encapsulates asingle methane molecule,has been synthesized for the first time.Methane is the first organic molecule,a swella st he largest, to have been encapsulated in C 60 to date.T he key orifice contraction step,aphotochemical desulfinylation of an open fullerene,w as completed, even though it is inhibited by the endohedral molecule.T he crystal structure of the nickel(II) octaethylporphyrin/ benzenesolvate shows no significant distortion of the carbon cage,r elative to the C 60 analogue,and shows the methane hydrogens as ashell of electron density around the central carbon, indicative of the quantum nature of the methane.The 1 Hspin-lattice relaxation times (T 1 )f or endohedral methane are similar to those observed in the gas phase,i ndicating that methane is freely rotating inside the C 60 cage.T he synthesis of CH 4 @C 60 opens ar oute to endofullerenes incorporating large guest molecules and atoms.Soon after the discovery of C 60 in 1985, [1] came recognition that its approximately spherical 3.7 diameter cavity provides aunique environment in which to isolate single atoms. [2] Since then endohedral fullerenes,that is,compounds denoted A@C 60 in which molecules or atoms are enclosed within the fullerene cage,have been the focus of substantial experimental and theoretical efforts. [3][4][5] Endohedral fullerenes may be synthesized by forming the fullerene in the presence of the endohedral species (particularly successful for metallofullerenes), [3,5] by high temperature and pressure treatment of the fullerene with the endohedral species (inert gas@C 60 ), [6,7] or by ion bombardment of the fullerene (N@C 60 ), [8] but all give very low incorporation and require extensive purification. Furthermore,t hese methods are not applicable to the incorporation of small organic molecules.Them acroscopic-scale preparation of endohedral fullerenes by multi-step "molecular surgery" [9][10][11][12] involves chemically opening an orifice in the fullerene,o fas ize suitable to allow entry of the single molecule.S uturing of this orifice to restore the pristine carbon cage was pioneered by Komatsu [13,14] and Murata [15] who reported the first syntheses of H 2 @C 60 and H 2 O@C 60 following insertion of H 2 or H 2 O under high-pressure,i nto open-cage fullerenes 1 and 2, respectively.O ptimized procedures for the synthesis of H 2 @C 60 and H 2 O@C 60 have subsequently been reported by ourselves, [16] based on Murataso pen-cage C 60 derivative 2, and also applied to the synthesis of HF@C 60 (Figure 1). [17,18] Them acroscopic quantities of endohedral fullerenes provided by molecular surgery have allowed detailed investigation of physical properties,i ncluding by neutron scattering, infrared spectroscopy,a nd NMR spectroscopy. [19] These methods have shown that, as ar esult of the inert and highly symmetrical environment of the cavity,a ne ntrapped molecule behaves much as would be expected in the very lowpressure gas state, [17,[19][20][21][22][23] displ...
[60]Fullerene‐based carbon nanopores were synthesized to enable the placement of two molecules of nitric oxide (NO) at an accurate distance from one another. A linear orientation of the two NO molecules inside the assembled nanopores was confirmed crystallographically. Theoretical studies suggested possible free rotation inside the carbon nanopore, while the two conformations of NO in which its long axis was oriented toward the orifice of the nanopore were predicted to be dominant. The paramagnetic shifts caused by NO showed a major contribution from the Fermi contact mechanism. The Solomon–Bloembergen theory was found to describe well the paramagnetic relaxation enhancement of a water molecule in a paired nanopore even under equilibrium as a result of fixing of the NO molecule with a distance of approximately 12 Å, thus demonstrating a long‐range bimolecular magnetic interaction.
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