Phenyl-C61-butyric acid methyl ester

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
CAS Number	160848-21-5 ; 160848-22-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	21170152 ;
PubChem CID	53384373;
CompTox Dashboard (EPA)	DTXSID80894348 ;
	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(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−1
Density	1.631 g/cm3 (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 nm α = 90°, β = 106.9°, γ = 90°
Formula units (Z)	4
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

PCBM ([6,6]-phenyl-C₆₁-butyric acid methyl ester) is a fullerene derivative being investigated for its potential use in organic solar cells.^[3]

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.

References

^ ^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.
^ 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.
^ 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.
^ 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.

[str-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 [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.

[3]

[1]

[2]

[4]

Names

PCBM crystal and its model. Gray: carbons, red: oxygens, white: hydrogens.
Preferred IUPAC name Methyl 4-[3′-Phenyl-3′H-cyclopropa[1,9](C₆₀-I_h)[5,6]fulleren-3′-yl]butanoate
Identifiers
CAS Number	160848-21-5^N 160848-22-6^N
3D model (JSmol)	Interactive image
ChemSpider	21170152^Y
PubChem CID	53384373
CompTox Dashboard (EPA)	DTXSID80894348
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^Y Key: FIGVSQKKPIKBST-UHFFFAOYSA-N^Y 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⁻¹
Density	1.631 g/cm³ (100 K)^[1]
Melting point	280 °C (536 °F; 553 K)(sublimates)^[2]
Structure(100 K)^[1]
Crystal structure	Monoclinic
Space group	P2(1)/n
Lattice constant	a = 1.347 nm, b = 1.51 nm, c = 1.901 nm α = 90°, β = 106.9°, γ = 90°
Formula units (Z)	4
Hazards
GHS labelling:
Pictograms
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Phenyl-C61-butyric acid methyl ester

See also

References