Methyl [6,6]-phenyl-C61-butyrate
[CAS# 160848-22-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Other ester compounds
• Name: Methyl [6,6]-phenyl-C61-butyrate
• Synonyms: 3'-Phenyl-3'H-cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-butanoic acid methyl ester; [6,6]PCBM; [60]PCBM
• Molecular Formula: C₇₂H₁₄O₂
• Molecular Weight: 910.88
• CAS Registry Number: 160848-22-6
• SMILES: COC(=O)CCCC1(C23C14c5c6c7c8c9c1c%10c%11c%12c%13c%10c%10c9c9c7c5c5c2c2c7c5c9c%10c5c%13c9c%10c%12c%12c%13c%11c%11c1c8c1c6c6c4c4c3c3c2c(c9c57)c2c%10c%12c5c7c%13c%11c1c6c7c4c5c23)c1ccccc1

Properties

• Density: 2.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 3.362, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

Methyl [6,6]-phenyl-C61-butyrate is a chemical compound that belongs to the fullerene family, which is composed of carbon molecules arranged in a spherical or ellipsoidal shape. It is a derivative of the fullerene C60 molecule, modified with a butyrate ester group and a phenyl group attached to the carbon skeleton. This compound has attracted attention in the fields of organic electronics, solar cells, and photovoltaics due to its unique properties and potential applications in energy conversion technologies.

The discovery of methyl [6,6]-phenyl-C61-butyrate dates back to the early 1990s when the fullerene C60 was first identified as a potential material for use in various electronic and optoelectronic applications. Fullerenes, particularly C60, have unique electronic properties that make them attractive candidates for use in organic solar cells, organic light-emitting diodes (OLEDs), and other electronic devices. In order to enhance the solubility and processability of fullerenes in solution, researchers began to explore various chemical modifications. One such modification was the attachment of butyrate ester groups to the C60 molecule, which led to the creation of methyl [6,6]-phenyl-C61-butyrate. This modification improved the material's solubility in organic solvents, making it easier to incorporate into electronic devices.

Methyl [6,6]-phenyl-C61-butyrate has become widely used in organic photovoltaics (OPVs), particularly in bulk-heterojunction solar cells. In these devices, the compound is commonly used as an electron acceptor material, working in combination with a suitable electron donor material to convert sunlight into electricity. The fullerene derivative acts as a crucial component in the active layer of the solar cell, where it helps facilitate the movement of charge carriers generated by light absorption. The electron acceptor properties of methyl [6,6]-phenyl-C61-butyrate allow it to efficiently capture electrons from the donor material, leading to the generation of an electrical current. The high efficiency of organic solar cells based on methyl [6,6]-phenyl-C61-butyrate has made it one of the most important materials in the development of flexible and low-cost solar cells.

In addition to its role in organic photovoltaics, methyl [6,6]-phenyl-C61-butyrate has also been investigated for use in organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). The compound's ability to act as an electron acceptor in various organic electronic devices makes it a versatile material for a range of optoelectronic applications. Furthermore, its relatively low cost of production and compatibility with solution-based processing techniques have made it a promising candidate for use in large-scale, printable electronics.

The applications of methyl [6,6]-phenyl-C61-butyrate extend beyond photovoltaics and optoelectronics. Researchers are also exploring its potential use in sensors, energy storage devices, and other emerging technologies. The compound's ability to transport charge efficiently and its stable electronic properties under various environmental conditions make it suitable for a wide range of advanced materials applications.

However, challenges remain in the optimization of methyl [6,6]-phenyl-C61-butyrate-based devices. While these materials show promise in terms of efficiency and scalability, further research is needed to improve their long-term stability, charge transport properties, and overall performance. Advances in the synthesis and processing of fullerene derivatives like methyl [6,6]-phenyl-C61-butyrate will be critical in overcoming these challenges and fully realizing the potential of organic electronics in various applications.