{{redirect-distinguish2|PCBM|the Passive Common Berthing Mechanism}} {{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464200892 | ImageFile1 = PCBM structure.svg | ImageSize1 = 235px | ImageSize2 = 250px | ImageFile2=PCBM crystal and its model.jpg | ImageCaption2 = PCBM crystal and its model. Gray: carbons, red: oxygens, white: hydrogens. | PIN = Methyl 4-[3′-Phenyl-3′''H''-cyclopropa[1,9](C<sub>60</sub>-''I''<sub>h</sub>)[5,6]fulleren-3′-yl]butanoate |Section1={{Chembox Identifiers | InChIKey1 = FIGVSQKKPIKBST-UHFFFAOYSA-N | ChemSpiderID = 21170152 | CASNo_Ref = {{cascite|changed|??}} | CASNo = 160848-21-5 | CASNo1 = 160848-22-6 | CASNo1_Ref = {{cascite|changed|??}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | PubChem = 53384373 | SMILES = COC(=O)CCCC1(C23C14C5=C6C7=C8C5=C9C1=C5C%10=C%11C%12=C%13C%10=C%10C1=C8C1=C%10C8=C%10C%14=C%15C%16=C%17C(=C%12C%12=C%17C%17=C%18C%16=C%16C%15=C%15C%10=C1C7=C%15C1=C%16C(=C%18C7=C2C2=C%10C(=C5C9=C42)C%11=C%12C%10=C%177)C3=C16)C%14=C%138)C1=CC=CC=C1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C72H14O2/c1-74-11(73)8-5-9-70(10-6-3-2-4-7-10)71-66-58-50-40-30-22-14-12-13-16-20-18(14)26-34-28(20)38-32-24(16)25-17(13)21-19-15(12)23(22)31-37-27(19)35-29(21)39-33(25)43-42(32)52-46(38)56-48(34)54(44(50)36(26)30)62(66)64(56)68-60(52)61-53(43)47(39)57-49(35)55-45(37)51(41(31)40)59(58)67(71)63(55)65(57)69(61)72(68,70)71/h2-4,6-7H,5,8-9H2,1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FIGVSQKKPIKBST-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=72 | H=14 | O=2 | Density=1.631 g/cm<sup>3</sup> (100 K)<ref name=str/> | MeltingPtC=280 | MeltingPt_ref=(sublimates)<ref>{{cite journal|title=Thermal [6,6] → [6,6] Isomerization and Decomposition of PCBM (Phenyl-C<sub>61</sub>-butyric Acid Methyl Ester)|journal=Chemistry of Materials|volume=26|issue=7|pages=2361–2367|doi=10.1021/cm500594u|year=2014|last1=Larson|first1=Bryon W.|last2=Whitaker|first2=James B.|last3=Popov|first3=Alexey A.|last4=Kopidakis|first4=Nikos|last5=Rumbles|first5=Garry|last6=Boltalina|first6=Olga V.|last7=Strauss|first7=Steven H.}}</ref> }} |Section5={{Chembox Structure | Structure_ref= (100 K)<ref name=str>{{cite journal|doi=10.1039/C3TC31075B|title=Micro-focused X-ray diffraction characterization of high-quality [6,6]-phenyl-C<sub>61</sub>-butyric acid methyl ester single crystals without solvent impurities|year=2013|journal=Journal of Materials Chemistry C|volume=1|issue=36|pages=5619–5623|url=https://zenodo.org/record/909936|last1=Paternò|first1=Giuseppe|last2=Warren|first2=Anna J.|last3=Spencer|first3=Jacob|last4=Evans|first4=Gwyndaf|last5=Sakai|first5=Victoria García|last6=Blumberger|first6=Jochen|last7=Cacialli|first7=Franco|doi-access=free}}</ref> | CrystalStruct = Monoclinic | SpaceGroup=P2(1)/n | LattConst_a = 1.347 nm | LattConst_b = 1.51 nm | LattConst_c = 1.901 nm | LattConst_alpha = | LattConst_beta = 106.9 | LattConst_gamma = | LattConst_ref = | LattConst_Comment = | UnitCellVolume = | UnitCellFormulas = 4 | Coordination = | MolShape = | OrbitalHybridisation = | Dipole = }} |Section7 = {{Chembox Hazards | GHSPictograms = {{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|319|335}} | PPhrases = {{P-phrases|261|264|271|280|304+340|305+351+338|312|337+313|403+233|405|501}} }} }}
'''PCBM''' ('''[6,6]-phenyl-C<sub>61</sub>-butyric acid methyl ester''') is a fullerene derivative being investigated for its potential use in organic solar cells.<ref>{{Cite journal |last1=Björström |first1=Cecilia |last2=Bernasik |first2=Andrzej |last3=Rysz |first3=Jakub |last4=Budkowski |first4=Andrzej |last5=Nilsson |first5=Svante |last6=Svensson |first6=Mattias |last7=Andersson |first7=Mats |last8=Magnusson |first8=Kjell |last9=Moons |first9=Ellen |author-link9=Ellen Moons |date=December 21, 2005 |title=Multilayer formation in spin-coated thin films of low-bandgap polyfluorene: PCBM blends |journal=Journal of Physics: Condensed Matter |volume=17 |issue=50 |pages=L529–L534 |doi=10.1088/0953-8984/17/50/L01}}</ref>
PCBM is a fullerene derivative of the C<sub>60</sub> buckyball that was first synthesized in the 1990s.<ref>{{cite journal|doi=10.1021/jo00108a012|title=Preparation and Characterization of Fulleroid and Methanofullerene Derivatives|year=1995|last1=Hummelen|first1=Jan C.|last2=Knight|first2=Brian W.|last3=Lepeq|first3=F.|last4=Wudl|first4=Fred|last5=Yao|first5=Jie|last6=Wilkins|first6=Charles L.|journal=The Journal of Organic Chemistry|volume=60|issue=3|pages=532–538}}</ref> It is an electron acceptor material and is often used in organic solar cells (plastic solar cells) or flexible electronics in conjunction with electron donor materials such as P3HT or other conductive polymers. It is a more practical choice for an electron acceptor when compared with fullerenes because of its solubility in chlorobenzene. This allows for solution processable donor/acceptor mixes, a necessary property for "printable" solar cells. However, considering the cost of fabricating fullerenes, it is not certain that this derivative can be synthesized on a large scale for commercial applications.
==See also== *Organic solar cell
==References== {{Commons category|PCBM}} {{Reflist}}
{{DEFAULTSORT:Phenyl-C61-Butyric Acid Methyl Ester}} Category:Carboxylate esters Category:Fullerenes Category:Phenyl compounds