Buckminsterfullerene
Buckminsterfullerene is a type of fullerene with the formula C60. It has a cage-like fused-ring structure (truncated icosahedron) made of twenty hexagons and twelve pentagons, and resembles a soccer ball. Each of its 60 carbon atoms is bonded to its three neighbors. Buckminsterfullerene is a black solid that dissolves in hydrocarbon solvents to produce a violet solution. The compound was discovered in 1985 and has received intense study, although few real world applications have been found. A co…
Jump to content Main menu Main menu move to sidebar hide Navigation Main page Contents Current events Random article About Wikipedia Contact us Contribute Help Learn to edit Community portal Recent changes Upload file Special pages Search Search Appearance Donate Create account Log in Personal tools Donate Create account Log in Contents move to sidebar hide (Top) 1 Occurrence 2 History Toggle History subsection 2.1 Etymology 3 Synthesis 4 Structure 5 Properties Toggle Properties subsection 5.1 Solution 5.2 Solid 6 Chemical reactions and properties Toggle Chemical reactions and properties subsection 6.1 Redox (electron-transfer reactions) 6.2 Hydrogenation 6.3 Halogenation 6.4 Addition of oxygen atoms 6.5 Cycloadditions 6.6 Free radical reactions 6.7 Cyclopropanation (Bingel reaction) 6.8 Redox reactions – C 60 anions and cations 6.8.1 C 60 anions 6.8.2 C 60 cations 6.9 Metal complexes 6.10 Endohedral fullerenes 7 Potential applications in technology 8 Potential applications in health Toggle Potential applications in health subsection 8.1 Ingestion and risks 8.2 Oils with C60 and risks 9 References 10 Bibliography 11 Further reading 12 External links Toggle the table of contents Buckminsterfullerene 34 languages العربية تۆرکجه Български བོད་ཡིག Bosanski Català Čeština Dansk Deutsch Ελληνικά Español فارسی Français Gaeilge हिन्दी Magyar Bahasa Indonesia Italiano 日本語 한국어 Македонски Nederlands Norsk nynorsk Norsk bokmål Polski Português Srpskohrvatski / српскохрватски Српски / srpski Svenska தமிழ் اردو Tiếng Việt 吴语 中文 Edit links Article Talk English Read Edit View history Tools Tools move to sidebar hide Actions Read Edit View history General What links here Related changes Upload file Permanent link Page information Cite this page Get shortened URL Switch to legacy parser Print/export Download as PDF Printable version In other projects Wikimedia Commons Wikidata item Appearance move to sidebar hide From Wikipedia, the free encyclopedia This is an old revision of this page, as edited by 2601:243:197f:3fb0f5ba:c256 ( talk ) at 15:11, 11 September 2023 . The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision . Revision as of 15:11, 11 September 2023 by 2601:243:197f:3fb0f5ba:c256 ( talk ) ( diff ) ← Previous revision | Latest revision ( diff ) | Newer revision → ( diff ) Cage-like allotrope of carbon "Buckyball" redirects here. For other uses, see Buckyball (disambiguation) . Buckminsterfullerene Names Pronunciation / ˌ b ʌ k m ɪ n s t ər ˈ f ʊ l ə r iː n / Preferred IUPAC name (C 60 - I h )5,6fullerene 1 Other names Buckyballs; Fullerene-C 60 ; 60fullerene Identifiers CAS Number 99685-96-8 Y 3D model ( JSmol ) Interactive image Beilstein Reference 5901022 ChEBI CHEBI:33128 Y ChemSpider 110185 Y ECHA InfoCard 100.156.884 PubChem CID 123591 UNII NP9U26B839 CompTox Dashboard ( EPA ) DTXSID4031772 InChI InChI=1S/C60/c1-2-5-6-3(1)8-12-10-4(1)9-11-7(2)17-21-13(5)23-24-14(6)22-18(8)28-20(12)30-26-16(10)15(9)25-29-19(11)27(17)37-41-31(21)33(23)43-44-34(24)32(22)42-38(28)48-40(30)46-36(26)35(25)45-39(29)47(37)55-49(41)51(43)57-52(44)50(42)56(48)59-54(46)53(45)58(55)60(57)59 Y Key: XMWRBQBLMFGWIX-UHFFFAOYSA-N Y InChI=1/C60/c1-2-5-6-3(1)8-12-10-4(1)9-11-7(2)17-21-13(5)23-24-14(6)22-18(8)28-20(12)30-26-16(10)15(9)25-29-19(11)27(17)37-41-31(21)33(23)43-44-34(24)32(22)42-38(28)48-40(30)46-36(26)35(25)45-39(29)47(37)55-49(41)51(43)57-52(44)50(42)56(48)59-54(46)53(45)58(55)60(57)59 Key: XMWRBQBLMFGWIX-UHFFFAOYAU InChI=1S/C60/c1-2-5-6-3(1)8-12-10-4(1)9-11-7(2)17-21-13(5)23-24-14(6)22-18(8)28-20(12)30-26-16(10)15(9)25-29-19(11)27(17)37-41-31(21)33(23)43-44-34(24)32(22)42-38(28)48-40(30)46-36(26)35(25)45-39(29)47(37)55-49(41)51(43)57-52(44)50(42)56(48)59-54(46)53(45)58(55)60(57)59 Key: XMWRBQBLMFGWIX-UHFFFAOYSA-N SMILES c12c3c4c5c2c2c6c7c1c1c8c3c3c9c4c4c%10c5c5c2c2c6c6c%11c7c1c1c7c8c3c3c8c9c4c4c9c%10c5c5c2c2c6c6c%11c1c1c7c3c3c8c4c4c9c5c2c2c6c1c3c42 Properties Chemical formula C 60 Molar mass 720.660 g·mol −1 Appearance Dark needle-like crystals Density 1.65 g/cm 3 Solubility in water insoluble in water Vapor pressure 0.4–0.5 Pa (T ≈ 800 K); 14 Pa (T ≈ 900 K) 2 Structure Crystal structure Face-centered cubic, cF1924 Space group Fm 3 m, No. 225 Lattice constant a = 1.4154 nm Hazards GHS labelling : Pictograms Signal word Warning Hazard statements H315 , H319 , H335 Precautionary statements P261 , P264 , P271 , P280 , P302+P352 , P304+P340 , P305+P351+P338 , P312 , P321 , P332+P313 , P337+P313 , P362 , P403+P233 , P405 , P501 Except where otherwise noted, data are given for materials in their standard state (at 25 °C 77 °F, 100 kPa). Y verify ( what is Y N ?) Infobox references Chemical compound Part of a series of articles on Nanomaterials Carbon nanotubes Synthesis Chemistry Mechanical properties Optical properties Applications Timeline Fullerenes Buckminsterfullerene C70 fullerene Chemistry Health impact Carbon allotropes Other nanoparticles Carbon quantum dots Carbon nanotube quantum dots Silicon quantum dots Cadmium-free quantum dots Quantum dots Aluminium oxide Cellulose Ceramic Cobalt oxide Copper Gold Iron Iron oxide Iron–platinum Lipid Platinum Silver Titanium dioxide Nanostructured materials Nanocomposite Nanofoam Nanoporous materials Nanocrystalline material Science portal Technology portal v t e Buckminsterfullerene is a type of fullerene with the formula C 60 . It has a cage-like fused-ring structure ( truncated icosahedron ) made of twenty hexagons and twelve pentagons , and resembles a soccer ball . Each of its 60 carbon atoms is bonded to its three neighbors. Buckminsterfullerene is a black solid that dissolves in hydrocarbon solvents to produce a violet solution. The compound was discovered in 1985 and has received intense study, although few real world applications have been found. A common, shortened name for buckminsterfullerene is buckyballs. 3 Occurrence Buckminsterfullerene is the most common naturally occurring fullerene. Small quantities of it can be found in soot . 4 5 It also exists in space . Neutral C 60 has been observed in planetary nebulae 6 and several types of star . 7 The ionised form, C 60 + , has been identified in the interstellar medium , 8 where it is the cause of several absorption features known as diffuse interstellar bands in the near-infrared. 9 History Further information: Fullerene Harold Kroto Many footballs have the same arrangement of polygons as buckminsterfullerene, C 60 . Theoretical predictions of buckminsterfullerene molecules appeared in the late 1960s and early 1970s. 10 11 12 13 It was first generated in 1984 by Eric Rohlfing, Donald Cox, and Andrew Kaldor 13 14 using a laser to vaporize carbon in a supersonic helium beam, although the group did not realize that buckminsterfullerene had been produced. In 1985 their work was repeated by Harold Kroto , James R. Heath , Sean C. O'Brien , Robert Curl , and Richard Smalley at Rice University , who recognized the structure of C 60 as buckminsterfullerene. 15 Concurrent but unconnected to the Kroto-Smalley work, astrophysicists were working with spectroscopists to study infrared emissions from giant red carbon stars. 16 17 18 Smalley and team were able to use a laser vaporization technique to create carbon clusters which could potentially emit infrared at the same wavelength as had been emitted by the red carbon star. 16 19 Hence, the inspiration came to Smalley and team to use the laser technique on graphite to generate fullerenes. Using laser evaporation of graphite the Smalley team found C n clusters (where n > 20 and even) of which the most common were C 60 and C 70 . A solid rotating graphite disk was used as the surface from which carbon was vaporized using a laser beam creating hot plasma that was then passed through a stream of high-density helium gas. 20 The carbon species were subsequently cooled and ionized resulting in the formation of clusters. Clusters ranged in molecular masses, but Kroto and Smalley found predominance in a C 60 cluster that could be enhanced further by allowing the plasma to react longer. They also discovered that C 60 is a cage-like molecule, a regular truncated icosahedron . 16 20 Kroto, Curl, and Smalley were awarded the 1996 Nobel Prize in Chemistry for their roles in the discovery of buckminsterfullerene and the related class of molecules, the fullerenes . 10 The experimental evidence, a strong peak at 720 atomic mass units , indicated that a carbon molecule with 60 carbon atoms was forming, but provided no structural information. The research group concluded after reactivity experiments, that the most likely structure was a spheroidal molecule. The idea was quickly rationalized as the basis of an icosahedral symmetry closed cage structure. Kroto mentioned geodesic dome structures of the noted futurist and inventor Buckminster Fuller as influences in the naming of this particular substance as buckminsterfullerene. 10 In 1989 physicists Wolfgang Krätschmer , Konstantinos Fostiropoulos , and Donald R. Huffman observed unusual optical absorptions in thin films of carbon dust (soot). The soot had been generated by an arc-process between two graphite electrodes in a helium atmosphere where the electrode material evaporates and condenses forming soot in the quenching atmosphere. Among other features, the IR spectra of the soot showed four discrete bands in close agreement to those proposed for C 60 . 21 22 Another paper on the characterization and verification of the molecular structure followed on in the same year (1990) from their thin film experiments, and detailed also the extraction of an evaporable as well as benzene -soluble material from the arc-generated soot. This extract had TEM and X-ray crystal analysis consistent with arrays of spherical C 60 molecules, approximately 1.0 nm in van der Waals diameter 23 as well as the expected molecular mass of 720 Da for C 60 (and 840 Da for C 70 ) in their mass spectra . 24 The method was simple and efficient to prepare the material in gram amounts per day (1990) which has boosted the fullerene research and is even today applied for the commercial production of fullerenes. The discovery of practical routes to C 60 led to the exploration of a new field of chemistry involving the study of fullerenes. Etymology The discoverers of the allotrope named the newfound molecule after Buckminster Fuller , who designed many geodesic dome structures that look similar to C 60 and who had died in 1983, the year before discovery. This is slightly misleading, however, as Fuller's geodesic domes are constructed only by further dividing hexagons or pentagons into triangles, which are then deformed by moving vertices radially outward to fit the surface of a sphere. 25 Geometrically speaking, buckminsterfullerene is a naturally-occurring example of a Goldberg polyhedron . A common, shortened name for buckminsterfullerene is buckyballs. 26 Synthesis Soot is produced by laser ablation of graphite or pyrolysis of aromatic hydrocarbons . Fullerenes are extracted from the soot with organic solvents using a Soxhlet extractor . 27 This step yields a solution containing up to 75% of C 60 , as well as other fullerenes. These fractions are separated using chromatography . 28 Generally, the fullerenes are dissolved in a hydrocarbon or halogenated hydrocarbon and separated using alumina columns. 29 Structure Buckminsterfullerene is a truncated icosahedron with 60 vertices , 32 faces (20 hexagons and 12 pentagons where no pentagons share a vertex), and 90 edges (60 edges between 5-membered & 6-membered rings and 30 edges are shared between 6-membered & 6-membered rings), with a carbon atom at the vertices of each polygon and a bond along each polygon edge. The van der Waals diameter of a C 60 molecule is about 1.01 nanometers (nm). The nucleus to nucleus diameter of a C 60 molecule is about 0.71 nm. The C 60 molecule has two bond lengths. The 6:6 ring bonds (between two hexagons) can be considered " double bonds " and are shorter than the 6:5 bonds (between a hexagon and a pentagon). Its average bond length is 0.14 nm. Each carbon atom in the structure is bonded covalently with 3 others. 30 A carbon atom in the C 60 can be substituted by a nitrogen or boron atom yielding a C 59 N or C 59 B respectively. 31 Energy level diagram for C 60 under "ideal" spherical (left) and "real" icosahedral symmetry (right). Properties Orthogonal projections Centered by Vertex Edge 5–6 Edge 6–6 Face Hexagon Face Pentagon Image Projective symmetry 2 2 2 6 10 For a time buckminsterfullerene was the largest known molecule observed to exhibit wave–particle duality ; theoretically every object exhibits this behavior. 32 In 2020 the dye molecule phthalocyanine exhibited the duality that is more famously attributed to light, electrons and other small particles and molecules. 33 Solution C 60 solution Solubility of C 60 34 35 36 Solvent Solubility (g/L) 1-chloronaphthalene 51 1-methylnaphthalene 33 1,2-dichlorobenzene 24 1,2,4-trimethylbenzene 18 tetrahydronaphthalene 16 carbon disulfide 8 1,2,3-tribromopropane 8 xylene 5 bromoform 5 cumene 4 toluene 3 benzene 1.5 carbon tetrachloride 0.447 chloroform 0.25 n - hexane 0.046 cyclohexane 0.035 tetrahydrofuran 0.006 acetonitrile 0.004 methanol 0.00004 water 1.3 × 10 −11 pentane 0.004 octane 0.025 isooctane 0.026 decane 0.070 dodecane 0.091 tetradecane 0.126 dioxane 0.0041 mesitylene 0.997 dichloromethane 0.254 Optical absorption spectrum of C 60 solution, showing diminished absorption for the blue (~450 nm) and red (~700 nm) light that results in the purple color. Fullerenes are sparingly soluble in aromatic solvents and carbon disulfide , but insoluble in water. Solutions of pure C 60 have a deep purple color which leaves a brown residue upon evaporation. The reason for this color change is the relatively narrow energy width of the band of molecular levels responsible for green light absorption by individual C 60 molecules. Thus individual molecules transmit some blue and red light resulting in a purple color. Upon drying, intermolecular interaction results in the overlap and broadening of the energy bands, thereby eliminating the blue light transmittance and causing the purple to brown color change. 16 C 60 crystallises with some solvents in the lattice ("solvates"). For example, crystallization of C 60 from benzene solution yields triclinic crystals with the formula C 60 ·4C 6 H 6 . Like other solvates, this one readily releases benzene to give the usual face-centred cubic C 60 . Millimeter-sized crystals of C 60 and C 70 can be grown from solution both for solvates and for pure fullerenes. 37 38 Solid Micrograph of C 60 . Packing of C 60 in crystal. In solid buckminsterfullerene, the C 60 molecules adopt the fcc ( face-centered cubic ) motif. They start rotating at about −20 °C. This change is associated with a first-order phase transition to an fcc structure and a small, yet abrupt increase in the lattice constant from 1.411 to 1.4154 nm. 39 C 60 solid is as soft as graphite , but when compressed to less than 70% of its volume it transforms into a superhard form of diamond (see aggregated diamond nanorod ). C 60 films and solution have strong non-linear optical properties; in particular, their optical absorption increases with light intensity (saturable absorption). C 60 forms a brownish solid with an optical absorption threshold at ≈1.6 eV. 40 It is an n-type semiconductor with a low activation energy of 0.1–0.3 eV; this conductivity is attributed to intrinsic or oxygen-related defects. 41 Fcc C 60 contains voids at its octahedral and tetrahedral sites which are sufficiently large (0.6 and 0.2 nm respectively) to accommodate impurity atoms. When alkali metals are doped into these voids, C 60 converts from a semiconductor into a conductor or even superconductor. 39 42 Chemical reactions and properties Redox (electron-transfer reactions) C 60 undergoes six reversible, one-electron reductions, ultimately generating C 6− 60 . Its oxidation is irreversible. The first reduction occurs at ≈-1.0 V ( Fc / Fc + ), showing that C 60 is a reluctant electron acceptor. C 60 tends to avoid having double bonds in the pentagonal rings, which makes electron delocalization poor, and results in C 60 not being " superaromatic ". C 60 behaves like an electron deficient alkene . For example, it reacts with some nucleophiles. 23 43 Hydrogenation C 60 exhibits a small degree of aromatic character, but it still reflects localized double and single C–C bond characters. Therefore, C 60 can undergo addition with hydrogen to give polyhydrofullerenes. C 60 also undergoes Birch reduction . For example, C 60 reacts with lithium in liquid ammonia, followed by tert -butanol to give a mixture of polyhydrofullerenes such as C 60 H 18 , C 60 H 32 , C 60 H 36 , with C 60 H 32 being the dominating product. This mixture of polyhydrofullerenes can be re-oxidized by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to give C 60 again. A selective hydrogenation method exists. Reaction of C 60 with 9,9′,10,10′-dihydroanthracene under the same conditions, depending on the time of reaction, gives C 60 H 32 and C 60 H 18 respectively and selectively. 44 C 60 can be hydrogenated, 45 suggesting that a modified buckminsterfullerene called organometallic buckyballs (OBBs) could become a vehicle for "high density, room temperature, ambient pressure storage of hydrogen ". These OBBs are created by binding atoms of a transition metal (TM) to C 60 or C 48 B 12 and then binding many hydrogen atoms to this TM atom, dispersing them evenly throughout the inside of the organometallic buckyball. The study found that the theoretical amount of H 2 that can be retrieved from the OBB at ambient pressure approaches 9 wt % , a mass fraction that has been designated as optimal for hydrogen fuel by the U.S. Department of Energy . citation needed Halogenation Addition of fluorine , chlorine , and bromine occurs for C 60 . Fluorine atoms are small enough for a 1,2-addition, while Cl 2 and Br 2 add to remote C atoms due to steric factors . For example, in C 60 Br 8 and C 60 Br 24 , the Br atoms are in 1,3- or 1,4-positions with respect to each other. Under various conditions a vast number of halogenated derivatives of C 60 can be produced, some with an extraordinary selectivity on one or two isomers over the other possible ones. Addition of fluorine and chlorine usually results in a flattening of the C 60 framework into a drum-shaped molecule. 44 Addition of oxygen atoms Solutions of C 60 can be oxygenated to the epoxide C 60 O. Ozonation of C 60 in 1,2-xylene at 257K gives an intermediate ozonide C 60 O 3 , which can be decomposed into 2 forms of C 60 O. Decomposition of C 60 O 3 at 296 K gives the epoxide, but photolysis gives a product in which the O atom bridges a 5,6-edge. 44 Cycloadditions The Diels–Alder reaction is commonly employed to functionalize C 60 . Reaction of C 60 with appropriate substituted diene gives the corresponding adduct. The Diels–Alder reaction between C 60 and 3,6-diaryl-1,2,4,5-tetrazines affords C 62 . The C 62 has the structure in which a four-membered ring is surrounded by four six-membered rings. A C 62 derivative C 62 (C 6 H 4 -4-Me) 2 synthesized from C 60 and 3,6-bis(4-methylphenyl)-3,6-dihydro-1,2,4,5-tetrazine The C 60 molecules can also be coupled through a 2+2 cycloaddition , giving the dumbbell-shaped compound C 120 . The coupling is achieved by high-speed vibrating milling of C 60 with a catalytic amount of KCN . The reaction is reversible as C 120 dissociates back to two C 60 molecules when heated at 450 K (177 °C; 350 °F) . Under high pressure and temperature, repeated 2+2