Phenyl-C61-butyric acid methyl ester

"PCBM" redirects here. It is 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-[3′-Phenyl-3′H-cyclopropa[1,9](C60-Ih)[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

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=CC=CC=CC1=C8C1=CC8=CC=CC=CC(=CC=CC=CC=CC=CC=C1C7=CC1=CC(=CC7=C2C2=CC(=C5C9=C42)C=CC=C7)C3=C16)C=C8)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 pictograms |
GHS Signal word | Warning

GHS hazard statements

| H319, H335

GHS precautionary statements

| P261, P264, P271, P280, P304+340, P305+351+338, P312, P337+313, P403+233, 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

Tracking categories (test):

* SizeSet

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.

## See also

* Organic solar cell

## References

1. ↑ 1.0 1.1 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. https://zenodo.org/record/909936.
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 et al. (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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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Phenyl-C61-butyric_acid_methyl_ester&oldid=4180328"
*[CID]: Compound ID
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P337+313]: Get medical advice/attention
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …