Phenyl-C61-butyric acid methyl ester

Phenyl-C61-butyric acid methyl ester

Names
Preferred IUPAC name Phenyl-C61-butyric acid methyl ester
Identifiers
CAS Number	160848-21-5
3D model (Jmol)	Interactive image
ChemSpider	21170152
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,5,8-9H2,1H3 Key: FIGVSQKKPIKBST-UHFFFAOYSA-N Key: FIGVSQKKPIKBST-UHFFFAOYSA-N
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
Properties
Chemical formula	C72H14O2
Molar mass	910.90 g·mol^−1
Structure
Crystal structure	Monoclinic, Space group: P2(1)/n[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.^[2]

PCBM is a fullerene derivative of the C₆₀ buckyball that was first synthesized in the 1990s by Fred Wudl's group.^[3] It is an electron acceptor material and is often used in plastic solar cells or flexible electronics in conjunction with electron donor materials such as P3HT or other 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

1. G.M.Paternò, A.Warren; J.Spencer, G.Evans; J.Blumberger, V.Garcia Sakai; F.Cacialli (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: 5619–5623. doi:10.1039/C3TC31075B.
2. 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.
3. 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.