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Phenyl-C61-butyric acid methyl ester

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"PCBM" redirects here. Not to be confused with the Passive Common Berthing Mechanism.
Phenyl-C61-butyric acid methyl ester

PCBM crystal and its model. Gray: carbons, red: oxygens, white: hydrogens.
Names
Preferred IUPAC name Methyl 4-(C60-Ih)fulleren-3′-yl]butanoate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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,5,8-9H2,1H3Key: FIGVSQKKPIKBST-UHFFFAOYSA-N
  • Key: FIGVSQKKPIKBST-UHFFFAOYSA-N
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
Properties
Chemical formula C72H14O2
Molar mass 910.902 g·mol
Density 1.631 g/cm (100 K)
Melting point 280 °C (536 °F; 553 K)(sublimates)
Structure(100 K)
Crystal structure Monoclinic
Space group P2(1)/n
Lattice constant a = 1.347 nm, b = 1.51 nm, c = 1.901 nmα = 90°, β = 106.9°, γ = 90°
Formula units (Z) 4
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H319, H335
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

PCBM (-phenyl-C61-butyric acid methyl ester) is a fullerene derivative being investigated for its potential use in organic solar cells.

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

References

  1. ^ 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 → 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.
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