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Phenyl-C61-butyric acid methyl ester

PCBM is the common abbreviation for the fullerene derivative [6,6]-phenyl-C61-butyric acid methyl ester. It is being investigated in organic solar cells.[3]

Phenyl-C61-butyric acid methyl ester

PCBM crystal and its model. Gray: carbons, red: oxygens, white: hydrogens.
Names
Preferred IUPAC name
Methyl 4-[3′-Phenyl-3′H-cyclopropa[1,9](C60-Ih)[5,6]fulleren-3′-yl]butanoate
Identifiers
  • 160848-21-5 N
  • 160848-22-6 N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 21170152 Y
  • 53384373
  • DTXSID80894348
  • InChI=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 Y
    Key: FIGVSQKKPIKBST-UHFFFAOYSA-N Y
  • Key: FIGVSQKKPIKBST-UHFFFAOYSA-N
  • 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
Properties
C72H14O2
Molar mass 910.902 g·mol−1
Density 1.631 g/cm3 (100 K)[1]
Melting point 280 °C (536 °F; 553 K)(sublimates)[2]
Structure(100 K)[1]
Monoclinic
P2(1)/n
a = 1.347 nm, b = 1.51 nm, c = 1.901 nm
α = 90°, β = 106.9°, γ = 90°
4
Hazards
GHS labelling:
Warning
H319, H335
P261, P264, P271, P280, P304+P340, P305+P351+P338, P312, P337+P313, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

PCBM is a fullerene derivative of the C60 buckyball that was first synthesized in the 1990s.[4] 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 edit

References edit

  1. ^ a b Paternò, Giuseppe; Warren, Anna J.; Spencer, Jacob; Evans, Gwyndaf; Sakai, Victoria García; Blumberger, Jochen; Cacialli, Franco (2013). "Micro-focused X-ray diffraction characterization of high-quality [6,6]-phenyl-C61-butyric acid methyl ester single crystals without solvent impurities". Journal of Materials Chemistry C. 1 (36): 5619–5623. doi:10.1039/C3TC31075B.
  2. ^ Larson, Bryon W.; Whitaker, James B.; Popov, Alexey A.; Kopidakis, Nikos; Rumbles, Garry; Boltalina, Olga V.; Strauss, Steven H. (2014). "Thermal [6,6] → [6,6] Isomerization and Decomposition of PCBM (Phenyl-C61-butyric Acid Methyl Ester)". Chemistry of Materials. 26 (7): 2361–2367. doi:10.1021/cm500594u.
  3. ^ Björström, Cecilia; Bernasik, Andrzej; Rysz, Jakub; Budkowski, Andrzej; Nilsson, Svante; Svensson, Mattias; Andersson, Mats; Magnusson, Kjell; Moons, Ellen (December 21, 2005). "Multilayer formation in spin-coated thin films of low-bandgap polyfluorene: PCBM blends". Journal of Physics: Condensed Matter. 17 (50): L529–L534. doi:10.1088/0953-8984/17/50/L01.
  4. ^ Hummelen, Jan C.; Knight, Brian W.; Lepeq, F.; Wudl, Fred; Yao, Jie; Wilkins, Charles L. (1995). "Preparation and Characterization of Fulleroid and Methanofullerene Derivatives". The Journal of Organic Chemistry. 60 (3): 532–538. doi:10.1021/jo00108a012.

phenyl, butyric, acid, methyl, ester, pcbm, redirects, here, confused, with, passive, common, berthing, mechanism, pcbm, common, abbreviation, fullerene, derivative, phenyl, butyric, acid, methyl, ester, being, investigated, organic, solar, cells, pcbm, crysta. PCBM redirects here Not to be confused with the Passive Common Berthing Mechanism PCBM is the common abbreviation for the fullerene derivative 6 6 phenyl C61 butyric acid methyl ester It is being investigated in organic solar cells 3 Phenyl C61 butyric acid methyl ester PCBM crystal and its model Gray carbons red oxygens white hydrogens NamesPreferred IUPAC name Methyl 4 3 Phenyl 3 H cyclopropa 1 9 C60 Ih 5 6 fulleren 3 yl butanoateIdentifiersCAS Number 160848 21 5 N160848 22 6 N3D model JSmol Interactive imageChemSpider 21170152 YPubChem CID 53384373CompTox Dashboard EPA DTXSID80894348InChI InChI 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 YKey FIGVSQKKPIKBST UHFFFAOYSA N YKey FIGVSQKKPIKBST UHFFFAOYSA NSMILES 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 C1PropertiesChemical formula C 72H 14O 2Molar mass 910 902 g mol 1Density 1 631 g cm3 100 K 1 Melting point 280 C 536 F 553 K sublimates 2 Structure 100 K 1 Crystal structure MonoclinicSpace group P2 1 nLattice constant a 1 347 nm b 1 51 nm c 1 901 nma 90 b 106 9 g 90 Formula units Z 4HazardsGHS labelling PictogramsSignal word WarningHazard statements H319 H335Precautionary statements P261 P264 P271 P280 P304 P340 P305 P351 P338 P312 P337 P313 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references PCBM is a fullerene derivative of the C60 buckyball that was first synthesized in the 1990s 4 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 editOrganic solar cellReferences edit nbsp Wikimedia Commons has media related to PCBM a b Paterno Giuseppe Warren Anna J Spencer Jacob Evans Gwyndaf Sakai Victoria Garcia Blumberger Jochen Cacialli Franco 2013 Micro focused X ray diffraction characterization of high quality 6 6 phenyl C61 butyric acid methyl ester single crystals without solvent impurities Journal of Materials Chemistry C 1 36 5619 5623 doi 10 1039 C3TC31075B Larson Bryon W Whitaker James B Popov Alexey A Kopidakis Nikos Rumbles Garry Boltalina Olga V Strauss Steven H 2014 Thermal 6 6 6 6 Isomerization and Decomposition of PCBM Phenyl C61 butyric Acid Methyl Ester Chemistry of Materials 26 7 2361 2367 doi 10 1021 cm500594u Bjorstrom Cecilia Bernasik Andrzej Rysz Jakub Budkowski Andrzej Nilsson Svante Svensson Mattias Andersson Mats Magnusson Kjell Moons Ellen December 21 2005 Multilayer formation in spin coated thin films of low bandgap polyfluorene PCBM blends Journal of Physics Condensed Matter 17 50 L529 L534 doi 10 1088 0953 8984 17 50 L01 Hummelen Jan C Knight Brian W Lepeq F Wudl Fred Yao Jie Wilkins Charles L 1995 Preparation and Characterization of Fulleroid and Methanofullerene Derivatives The Journal of Organic Chemistry 60 3 532 538 doi 10 1021 jo00108a012 Retrieved from https en wikipedia org w index php title Phenyl C61 butyric acid methyl ester amp oldid 1139180286, wikipedia, wiki, book, books, library,

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