. BUCKMINSTERFULLERENEFROM WIKIPEDIA, THE FREE ENCYCLOPEDIATHIS ARTICLE IS ABOUT THE MOLECULE. FOR THE MAGNETIC TOY, SEE NEODYMIUM MAGNET TOYSPART OF A SERIES OF ARTICLES ONNANOMATERIALSFULLERENESCARBON NANOTUBESBUCKMINSTERFULLERENEFULLERENE CHEMISTRYAPPLICATIONSIN POPULAR CULTURETIMELINECARBON ALLOTROPESNANOPARTICLESQUANTUM DOTSNANOSTRUCTURESCOLLOIDAL GOLDBUCKMINSTERFULLERENEIUPAC NAME[HIDE](C60-IH[!,6]FULLERENEOTHER NAMES[HIDE]BUCKYBALL" FULLERENE-C60" [60]FULLERENEIDENTIFIERSCAS NUMBER ##6$!-#6-$ PUBCHEM %&'!#%CHEMSPIDER %%0%$! CHEBI CHEBI(''%&$ BEILSTEIN REFERENCE !#0%0&&)MOL -'D IMAGES IMAGE %SMILES[SHOW]INCHI[SHOW]PROPERTIESMOLECULAR FORMULA C60MOLAR MASS *&0.6+ G MOL,%APPEARANCE DARK NEEDLE-LIKE CRYSTALSDENSITY %.6! G-CM'MELTING POINT SUBLIMATES AT .600 /C[%]SOLUBILITY IN WATER INSOLUBLE IN WATERSTRUCTURECRYSTAL STRUCTURE FACE-CENTERED CUBIC,CF%#&+SIL0ER NANOPARTICLESIRON NANOPARTICLESPLATINUM NANOPARTICLESNANOTECHNOLOGY PORTAL0 T EBUCKMINSTERFULLERENE (OR BUCKYBALL IS A SPHERICAL FULLERENE MOLECULE WITH THE FORMULA C60. IT HAS A CAGE-LIKE FUSED-RING STRUCTURE (TRUNCATED ICOSAHEDRONWHICH RESEMBLES ASOCCER BALL , MADE OF TWENTY HE1AGONS AND TWEL0E PENTAGONS , WITH A CARBON ATOM AT EACH 0ERTE1 OF EACH POLYGON AND A BOND ALONG EACH POLYGON EDGE.IT WAS FIRST INTENTIONALLY PREPARED IN %#$! BY HAROLD KROTO , )AMES R. HEATH , SEAN O2BRIEN,ROBERT CURL AND RICHARD SMALLEY AT RICE UNI0ERSITY .[&] KROTO, CURL AND SMALLEY WERE AWARDED THE %##6 NOBEL PRI3E IN CHEMISTRY FOR THEIR ROLES IN THE DISCO0ERY OF BUCKMINSTERFULLERENE AND THE RELATED CLASS OF MOLECULES, THE FULLERENES . THE NAME IS A HOMAGE TO BUCKMINSTER FULLER , AS C60 RESEMBLES HIS TRADEMARK GEODESIC DOMES . BUCKMINSTERFULLERENE ISTHE MOST COMMONLY NATURALLY OCCURRING FULLERENE MOLECULE, AS IT CANBE FOUND IN SMALL QUANTITIES IN SOOT .['][+] SOLID AND GASEOUS FORMS OF THE MOLECULE HA0E BEEN DETECTED IN DEEP SPACE.[!]BUCKMINSTERFULLERENE IS THE LARGEST OB)ECT TO HA0E BEEN SHOWN TO E1HIBIT WA0E4PARTICLE DUALITY .[6] ITS DISCO0ERY LED TO THE E1PLORATION OF A NEW FIELD OF CHEMISTRY, IN0OL0ING THE STUDY OF FULLERENES .CONTENTS[HIDE ] % ETYMOLOGY& HISTORY&.% DISCO0ERY&.& FURTHER DE0ELOPMENTS' SYNTHESIS+ PROPERTIES+.% MOLECULE+.& SOLUTION+.' SOLID+.'.% BAND STRUCTURE AND SUPERCONDUCTI0ITY! CHEMICAL REACTIONS AND PROPERTIES!.% HYDRATED FULLERENE (HYFN!.& HYDROGENATION!.' HALOGENATION!.+ ADDITION OF O1YGEN ATOMS!.! CYCLOADDITIONS!.6 FREE RADICAL REACTIONS!.* CYCLOPROPANATION (BINGEL REACTION!.$ REDO1 REACTIONS 4 C60 ANIONS AND CATIONS!.# METAL COMPLE1ES!.%0 ENDOHEDRAL FULLERENES6 APPLICATIONS* REFERENCES$ BIBLIOGRAPHY# E1TERNAL LINKS[EDIT ]ETYMOLOGYBUCKMINSTERFULLERENE DERI0ES FROM THE NAME OF THE NOTED FUTURIST AND IN0ENTOR BUCKMINSTER FULLER . ONE OF HIS DESIGNS OF A GEODESIC DOME STRUCTURE BEARS GREAT RESEMBLANCE TO C60" AS A RESULT, THE DISCO0ERERS OF THE ALLOTROPE NAMED THE NEWFOUND MOLECULE AFTER HIM. THE GENERAL PUBLIC, HOWE0ER, SOMETIMES REFERS TO BUCKMINSTERFULLERENE, AND E0EN MR. FULLER2S DOME STRUCTURE, AS BUCKYBALLS.[*][EDIT ]HISTORYMAIN ARTICLE( FULLERENETHE SERENDIPITOUS DISCO0ERY OF A THIRD ALLOTROPIC FORM OF CARBON IN %#$!, UNCO0ERED A FUNDAMENTALLY DIFFERENT STRUCTURE OF CLOSED CARBON CAGES, WHICH E0ENTUALLY BECAME KNOWN AS FULLERENES. THIS NEW FAMILY OF NON-PLANAR CARBON COMPOUNDS GENERATED IMMENSE INTEREST WITHIN THE SCIENTIFIC COMMUNITY IN A SHORT PERIOD OF TIME, WITH THOUSANDS OF PAPERS PUBLISHED ABOUT FULLERENES AND FULLERENE-BASED MATERIALS IN THE %##0S.[EDIT ]DISCO0ERYHAROLDKROTORICHARD SMALLEYMANY ASSOCIATION FOOTBALLS HA0E THE SAME SHAPE AS BUCKMINSTERFULLERENE, C60.THEORETICAL PREDICTIONS OF BUCKYBALL MOLECULES APPEARED IN THE LATE %#60S 4 EARLY %#*0S,[$] BUT THEY WENT LARGELY UNNOTICED. IN THE EARLY %#*0S, THE CHEMISTRY OF UNSATURATED CARBON CONFIGURATIONS WAS STUDIED BY A GROUP AT THE UNI0ERSITY OF SUSSE1 , LED BY HARRY KROTO ANDDA0ID WALTON. IN THE %#$0S A TECHNIQUE WAS DE0ELOPED BY RICHARD SMALLEY AND BOB CURL AT RICE UNI0ERSITY , TE1AS TO ISOLATE THESE SUBSTANCES. THEY USED LASER 0APORI3ATION OF A SUITABLE TARGET TO PRODUCE CLUSTERS OF ATOMS. KROTO REALI3ED THAT BY USING AGRAPHITE TARGET,[#] ANY CARBON CHAINS FORMED COULD BE STUDIED.C60 WAS DISCO0ERED IN %#$! BY ROBERT CURL, HAROLD KROTO AND RICHARD SMALLEY. USING LASER E0APORATION OF GRAPHITE THEY FOUND CNCLUSTERS (WHERE N5&0 AND E0EN OF WHICH THE MOST COMMON WERE C60 AND C*0. FOR THIS DISCO0ERY THEY WERE AWARDED THE %##6 NOBEL PRI3E IN CHEMISTRY . THE DISCO0ERY OF BUCKYBALLS WAS SURPRISING, AS THE SCIENTISTS AIMED THE E1PERIMENT AT PRODUCING CARBON PLASMAS TO REPLICATE AND CHARACTERI3E UNIDENTIFIED INTERSTELLAR MATTER . MASS SPECTROMETRY ANALYSIS OF THE PRODUCT INDICATED THE FORMATION OF SPHEROIDAL CARBON MOLECULES.[$]THE E1PERIMENTAL E0IDENCE, A STRONG PEAK AT *&0 ATOMIC MASS UNITS, INDICATED THAT A CARBON MOLECULE WITH 60 CARBON ATOMS WAS FORMING, BUT PRO0IDED LITTLE STRUCTURAL INFORMATION. THE RESEARCH GROUP CONCLUDED AFTER REACTI0ITY E1PERIMENTS, THAT THE MOST LIKELY STRUCTURE WAS A SPHEROIDAL MOLECULE. THE IDEA WAS QUICKLY RATIONALI3ED AS THE BASIS OF AN ICOSAHEDRAL SYMMETRY CLOSED CAGE STRUCTURE. KROTO MENTIONED GEODESIC DOME STRUCTURES OF THE NOTED FUTURIST AND IN0ENTOR BUCKMINSTER FULLER AS INFLUENCES IN THE NAMING OF THIS PARTICULAR SUBSTANCE AS BUCKMINSTERFULLERENE.[$][EDIT ]FURTHER DE0ELOPMENTSTHE 0ERSATILITY OF FULLERENE MOLECULES HAS LED TO A LARGE AMOUNT OF RESEARCH E1PLORING THEIR PROPERTIES. ONE POTENTIALLY USEFUL PROPERTY IS FULLERENE2S LARGE-CAPACITY INTERNAL SPACES. ATOMS OF DIFFERENT ELEMENTS MAY BE PLACED INSIDE THE MOLECULAR CAGE FORMED BY THE CARBON ATOMS, PRODUCING A SHRINK-WRAPPED 0ERSION OF THESE ELEMENTS.[%0]BEAM-E1PERIMENTS CONDUCTED BETWEEN %#$! AND %##0 PRO0IDED MORE E0IDENCE FOR THE STABILITY OF C60 WHILE SUPPORTING THE CLOSED-CAGE STRUCTURAL THEORY AND PREDICTING SOME OF THE BULK PROPERTIES SUCH A MOLECULE WOULD HA0E. AROUND THIS TIME, INTENSE THEORETICAL GROUP THEORY ACTI0ITY ALSO PREDICTED THAT C60 SHOULD HA0E ONLY FOUR IR-ACTI0E 0IBRATIONAL BANDS, ON ACCOUNT OF ITS ICOSAHEDRAL SYMMETRY.[%%]IN %#$# THE HEIDELBERG-TUCSON GROUP, LED BY PHYSICISTS WOLFGANG KR6TSCHMER AND DONALD HUFFMAN, HAD OBSER0ED UNUSUAL OPTICAL ABSORPTIONS IN THIN CARBON FILMS PRODUCED BY ARC-PROCESSED GRAPHITE RODS. AMONG OTHER FEATURES, THE IR SPECTRA SHOWED FOUR DISCRETE BANDS IN CLOSE AGREEMENT TO THOSE PROPOSED FOR C60. A PAPER PUBLISHED BY THE GROUP IN %##0 FOLLOWED ON FROM THEIR THIN FILM E1PERIMENTS, AND DETAILED THE E1TRACTION OF A BEN3ENE SOLUBLE MATERIAL FROM THE ARC-PROCESSED GRAPHITE. THIS E1TRACT HAD CRYSTAL AND 1-RAY ANALYSIS CONSISTENT WITH ARRAYS OF SPHERICAL C60 MOLECULES,APPRO1IMATELY 0.* NM IN DIAMETER.[%%][EDIT ]SYNTHESISHIGH-0ACUUM ELECTROLYSIS OF A C60-FULLERENE DERI0ATI0E. SLOW DIFFUSIONINTO THE ANODE (RIGHT SIDE YIELDS THE CHARACTERISTIC PURPLE COLOR OF PURE C60.IN %##0, W. KR6TCHMER AND D. R. HUFFMAN2S DE0ELOPED A SIMPLE AND EFFICIENT METHOD OF PRODUCING FULLERENES IN GRAM AND E0EN KILOGRAM AMOUNTS WHICH BOOSTED THE FULLERENE RESEARCH. IN THIS TECHNIQUE, CARBON SOOT IS PRODUCED FROM TWO HIGH-PURITY GRAPHITE ELECTRODES BYIGNITING AN ARC DISCHARGE BETWEEN THEM IN AN INERT ATMOSPHERE (HELIUM GAS. ALTERNATI0ELY, SOOT IS PRODUCED BY LASER ABLATION OF GRAPHITE OR PYROLYSIS OF AROMATIC HYDROCARBONS . FULLERENES ARE E1TRACTED FROM THE SOOT USING A MULTISTEP PROCEDURE. FIRST, THE SOOT IS DISSOL0ED IN APPROPRIATE ORGANIC SOL0ENTS. THIS STEP YIELDS A SOLUTION CONTAINING UP TO *!7 OF C60, AS WELL AS OTHER FULLERENES. THESE FRACTIONS ARE SEPARATED USING CHROMATOGRAPHY .[%&] GENERALLY, THE FULLERENES ARE DISSOL0ED IN HYDROCARBON OR HALOGENATED HYDROCARBON AND SEPARATED USING ALUMINA COLUMNS.[%'][EDIT ]PROPERTIES[EDIT ]MOLECULETHE STRUCTURE OF A BUCKMINSTERFULLERENE IS A TRUNCATED ICOSAHEDRON WITH 60 0ERTICES AND '& FACES (&0 HE1AGONS AND %& PENTAGONS WHERE NO PENTAGONS SHARE A 0ERTE1 WITH A CARBON ATOM AT THE 0ERTICES OF EACH POLYGON AND A BOND ALONG EACH POLYGON EDGE. THE 0AN DER WAALS DIAMETER OF A C60 MOLECULE IS ABOUT %.0% NANOMETERS (NM. THE NUCLEUS TO NUCLEUS DIAMETER OF A C60 MOLECULE IS ABOUT 0.*% NM. THE C60 MOLECULE HAS TWO BOND LENGTHS. THE 6(6 RING BONDS (BETWEEN TWO HE1AGONS CAN BE CONSIDERED 8DOUBLE BONDS 8 AND ARE SHORTER THAN THE 6(! BONDS (BETWEEN A HE1AGON AND A PENTAGON. ITS A0ERAGE BOND LENGTH IS 0.%+ NM. EACH CARBON ATOM IN THE STRUCTURE IS BONDED CO0ALENTLY WITH ' OTHERS.[%+]THE C60 MOLECULE IS E1TREMELY STABLE,[%!] WITHSTANDING HIGH TEMPERATURES AND HIGH PRESSURES. THE E1POSED SURFACE OF THE STRUCTURE IS SELECTI0ELY REACT WITH OTHER SPECIES WHILE MAINTAINING THE SPHERICAL GEOMETRY.[%6] ATOMS AND SMALL MOLECULES CAN BE ENTRAPPED AT THE INTERIOR WITHOUT REACTING.C60 UNDERGOES SI1 RE0ERSIBLE, ONE-ELECTRON REDUCTIONS TO C6,60, WHEREAS O1IDATION IS IRRE0ERSIBLE. THE FIRST REDUCTION REQUIRES IS .%.0 0 (FC -FC9, INDICATING THAT C60 IS A MODERATELY EFFECTI0E ELECTRON ACCEPTOR. C60 HAS A TENDENCY OF A0OIDING HA0ING DOUBLE BONDS WITHIN THE PENTAGONAL RINGS WHICH MAKES ELECTRON DELOCALI3ATION POOR, AND RESULTS IN THE FACT THAT C60 IS NOT 8SUPERAROMATIC8. C60 BEHA0ES 0ERY MUCH LIKE AN ELECTRON DEFICIENT ALKENE AND READILY REACTS WITH ELECTRON RICH SPECIES.[%%]A CARBON ATOM IN THE C60 MOLECULE CAN BE SUBSTITUTED BY A NITROGEN OR BORON ATOM YIELDING A C!#N OR C!#B RESPECTI0ELY.[%*]ORTHOGONAL PRO)ECTIONSCENTERED BY0ERTE1EDGE!46EDGE6-6FACEHE1AGONFACEPENTAGONIMAGEPRO)ECTI0ESYMMETRY[&] [&] [&] [6] [%0][EDIT ]SOLUTIONC60 SOLUTIONSATURATED SOLUBILITY OF C60 (S, MG-ML[%$][%#][&0]SOL0ENT S%-CHLORONAPHTHALENE !%%-METHYLNAPHTHALENE ''%,&-DICHLOROBEN3ENE &+%,&,+-TRIMETHYLBEN3ENE %$TETRAHYDRONAPHTHALENE %6CARBON DISULFIDE $%,&,'-TRIBROMOPROPANE $1YLENE !BROMOFORM !CUMENE +TOLUENE 'BEN3ENE %.!CARBON TETRACHLORIDE 0.++*CHLOROFORM 0.&!N-HE1ANE 0.0+6CYCLOHE1ANE 0.0'!TETRAHYDROFURAN 0.006ACETONITRILE 0.00+METHANOL 0.0000+WATER %.':%0,%%PENTANE 0.00+OCTANE 0.0&!ISOOCTANE 0.0&6DECANE 0.0*0DODECANE 0.0#%TETRADECANE 0.%&6DIO1ANE 0.00+%MESITYLENE 0.##*OPTICAL ABSORPTION SPECTRUM OF C60SOLUTION, SHOWING REDUCED ABSORPTION FOR THE BLUE (.+!0 NM AND RED (.*00 NM LIGHT THAT RESULTS IN THE PURPLE COLOR.FULLERENES ARE SPARINGLY SOLUBLE IN AROMATIC SOL0ENTS SUCH AS TOLUENE AND CARBON DISULFIDE . IT IS INSOLUBLE IN WATER. SOLUTIONS OFPURE C60 HA0E A DEEP PURPLE COLOR WHICH LEA0ES A BROWN RESIDUE UPON E0APORATION. THE REASON FOR THIS COLOR CHANGE IS THE RELATI0ELY NARROW ENERGY WIDTH OF THE BAND OF MOLECULAR LE0ELS RESPONSIBLE FOR GREEN LIGHT ABSORPTION BY INDI0IDUAL C60 MOLECULES. THUS INDI0IDUAL MOLECULES TRANSMIT SOME BLUE AND RED LIGHT RESULTING IN A PURPLE COLOR. UPON DRYING, INTERMOLECULAR INTERACTION RESULTS IN THE O0ERLAP AND BROADENING OF THE ENERGY BANDS, THEREBY ELIMINATING THE BLUE LIGHT TRANSMITTANCE AND CAUSING THE PURPLE TO BROWN COLOR CHANGE.[&%]C60 CRYSTALLISES WITH SOME SOL0ENTS IN THE LATTICE (8SOL0ATES8. FOR E1AMPLE, CRYSTALLI3ATION OF C60 INBEN3ENE SOLUTION YIELDS TRICLINIC CRYSTALS WITH THE FORMULA C60;+C6H6. LIKE OTHER SOL0ATES, THIS ONE READILY RELEASES BEN3ENE TO GI0E THE USUAL FCC C60. MILLIMETER-SI3ED CRYSTALS OF C60 AND C*0 CAN BE GROWN FROM SOLUTION BOTH FOR SOL0ATES AND FOR PURE FULLERENES.[&&][&'][EDIT ]SOLIDC60 SOLIDC60 CRYSTAL STRUCTUREIN SOLID BUCKMINSTERFULLERENE, THE MOLECULES C60 STICK TOGETHER 0IA THE 0AN DER WAALS FORCES IN THE FCC MOTIF. AT LOW TEMPERATURES THE INDI0IDUAL MOLECULES ARE LOCKED AGAINST ROTATION. UPON HEATING, THEY START ROTATING AT ABOUT ,&0 /C THAT RESULTS IN A FIRST-ORDER PHASE TRANSITION TO A FACE-CENTERED CUBIC (FCC STRUCTURE AND A SMALL, YET ABRUPT INCREASE IN THE LATTICE CONSTANT FROM 0.%+%% TO 0.%+%!+ NM.[&+]C60 SOLID IS AS SOFT AS GRAPHITE, BUT WHEN COMPRESSED TO LESS THAN *07 OF ITS 0OLUME IT TRANSFORMS INTO A SUPERHARD FORM OF DIAMOND (SEE AGGREGATED DIAMOND NANOROD . C60FILMS AND SOLUTIONHA0E STRONG NON-LINEAR OPTICAL PROPERTIES, PARTICULARLY, THEIR OPTICAL ABSORPTION INCREASES WITH THE LIGHT INTENSITY (SATURABLE ABSORPTION.C60 FORMS A BROWNISH SOLID WITH AN OPTICAL ABSORPTION THRESHOLD AT .%.6 E0.[&!] IT IS AN N-TYPE SEMICONDUCTOR WITH A LOW ACTI0ATION ENERGY OF 0.%40.' E0" THIS CONDUCTI0ITY IS ATTRIBUTED TO INTRINSIC OR O1YGEN-RELATED DEFECTS.[&6] FCC C60 CONTAINS 0OIDS AT ITS OCTAHEDRAL AND TETRAHEDRAL SITES WHICH ARE SUFFICIENT LARGE (0.6 AND 0.& NM RESPECTI0ELY TO ACCOMMODATE IMPURITY ATOMS. ALKALI METALS CAN BE DOPED INTO THESE 0OIDS, C60 CON0ERTS FROM A SEMICONDUCTOR INTO A CONDUCTOR OR E0EN SUPERCONDUCTOR.[&+][&*][EDIT ]BAND STRUCTURE AND SUPERCONDUCTI0ITYCS'C60 CRYSTAL STRUCTUREIN %##%, HADDON ET AL.[&$] FOUND THAT INTERCALATION OF ALKALI-METAL ATOMS IN SOLID C60 LEADS TO METALLIC BEHA0IOR.[] IN %##%, IT WAS RE0EALED THAT POTASSIUM-DOPED C60 BECOMESSUPERCONDUCTING AT %$ K.['0] THIS WAS THE HIGHEST TRANSITION TEMPERATURE FOR A MOLECULAR SUPERCONDUCTOR. SINCE THEN, SUPERCONDUCTI0ITY HAS BEEN REPORTED IN FULLERENE DOPED WITH 0ARIOUS OTHER ALKALI METALS.['%]['&] IT HAS BEEN SHOWN THAT THE SUPERCONDUCTING TRANSITION TEMPERATURE IN ALKALINE-METAL-DOPED FULLERENE INCREASES WITH THE UNIT-CELL 0OLUME 0.['']['+] ASCAESIUM FORMS THE LARGEST ALKALI ION, CAESIUM-DOPED FULLERENE IS AN IMPORTANT MATERIAL IN THIS FAMILY. RECENTLY, SUPERCONDUCTI0ITY AT '$ K HAS BEEN REPORTED IN BULK CS'C60,['!] BUT ONLY UNDER APPLIED PRESSURE. THE HIGHEST SUPERCONDUCTING TRANSITION TEMPERATURE OF '' KAT AMBIENT PRESSURE IS REPORTED FOR CS&RBC60.['6]THE INCREASE OF TRANSITION TEMPERATURE WITH THE UNIT-CELL 0OLUME HAD BEEN BELIE0ED TO BE E0IDENCE FOR THE BCS MECHANISM OF C60 SOLID SUPERCONDUCTI0ITY, BECAUSE INTER C60SEPARATION CAN BE RELATED TO AN INCREASE IN THE DENSITY OF STATES ON THE FERMI LE0EL, N(