| Revision as of 12:10, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 438224066 of page Phenyl-C61-butyric_acid_methyl_ester for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 00:13, 21 September 2024 edit Innerstream (talk | contribs)Autopatrolled, Extended confirmed users3,898 editsNo edit summary |
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{{redirect-distinguish2|PCBM|the Passive ]}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 428240663 |
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| verifiedrevid = 464200892 |
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| ImageFile = PCBM.png |
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| ImageFile1 = PCBM structure.svg |
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| ImageSize = 244 |
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| ImageSize1 = 235px |
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| ImageSize2 = 250px |
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| ImageName = Structural formula of phenyl-C61-butyric acid methyl ester |
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| ImageFile2=PCBM crystal and its model.jpg |
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| PIN = Phenyl-C61-butyric acid methyl ester |
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| ImageCaption2 = PCBM crystal and its model. Gray: carbons, red: oxygens, white: hydrogens. |
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| SystematicName = |
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| PIN = Methyl 4-(C<sub>60</sub>-''I''<sub>h</sub>)fulleren-3′-yl]butanoate |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChIKey1 = FIGVSQKKPIKBST-UHFFFAOYSA-N |
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| InChIKey1 = FIGVSQKKPIKBST-UHFFFAOYSA-N |
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| ChemSpiderID = 21170152 |
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| ChemSpiderID = 21170152 |
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| CASNo_Ref = {{cascite|changed|??}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = |
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| CASNo = 160848-21-5 |
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| InChI1 = |
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| CASNo1 = 160848-22-6 |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| SMILES = COC(=O)CCCC1(C23=C14c5c6c7c8c9c1c%10c%11c%12c%13c%14c%10c%10c9c7c7c5c5c2c2c9c%15c(c%13c%13c%12c%12c%16c%11c1c1c8c8c6c4c4c6c8c1c%16c1c%12c8c%13c%15c%11c8c(c16)c4c3c%112)c1c%14c%10c7c5c19)c1ccccc1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 53384373 |
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| 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 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FIGVSQKKPIKBST-UHFFFAOYSA-N |
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| StdInChIKey = FIGVSQKKPIKBST-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 72 |
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| C=72 | H=14 | O=2 |
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| Density=1.631 g/cm<sup>3</sup> (100 K)<ref name=str/> |
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| H = 14 |
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| MeltingPtC=280 |
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| O = 2 |
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| MeltingPt_ref=(sublimates)<ref>{{cite journal|title=Thermal → 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> |
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| ExactMass = 910.099379692 g mol<sup>−3</sup>}} |
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}} |
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}} |
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|Section5={{Chembox Structure |
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| Structure_ref= (100 K)<ref name=str>{{cite journal|doi=10.1039/C3TC31075B|title=Micro-focused X-ray diffraction characterization of high-quality -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> |
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| CrystalStruct = Monoclinic |
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| SpaceGroup=P2(1)/n |
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| LattConst_a = 1.347 nm |
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| LattConst_b = 1.51 nm |
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| LattConst_c = 1.901 nm |
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| LattConst_alpha = |
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| LattConst_beta = 106.9 |
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| LattConst_gamma = |
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| LattConst_ref = |
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| LattConst_Comment = |
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| UnitCellVolume = |
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| UnitCellFormulas = 4 |
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| Coordination = |
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| MolShape = |
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| OrbitalHybridisation = |
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| Dipole = |
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}} |
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|Section7 = {{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|304+340|305+351+338|312|337+313|403+233|405|501}} |
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}} |
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}} |
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'''PCBM''' ('''-phenyl-C<sub>61</sub>-butyric acid methyl ester''') is a ] being investigated for its potential use in ] ].<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> |
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PCBM is a ] of the C<sub>60</sub> ] 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 ] material and is often used in ]s (plastic solar cells) or flexible electronics in conjunction with ] materials such as ] or other ]s. It is a more practical choice for an electron acceptor when compared with fullerenes because of its solubility in ]. 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. |
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==See also== |
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*] |
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==References== |
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{{Commons category|PCBM}} |
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{{Reflist}} |
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{{DEFAULTSORT:Phenyl-C61-Butyric Acid Methyl Ester}} |
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] |
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] |
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] |