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![]() PCBM crystal and its model. Gray: carbons, red: oxygens, white: hydrogens. | |
Names | |
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Preferred IUPAC name Methyl 4-[3′-Phenyl-3′H-cyclopropa[1,9](C60-Ih)[5,6]fulleren-3′-yl]butanoate | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
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] | |
Monoclinic | |
P2(1)/n | |
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: | |
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Warning | |
H319, H335 | |
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). |
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. [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.
A fullerene is an allotrope of carbon whose molecule consists of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to seven atoms. The molecule may be a hollow sphere, ellipsoid, tube, or many other shapes and sizes. Graphene, which is a flat mesh of regular hexagonal rings, can be seen as an extreme member of the family.
Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals or amorphous thin films. In general, they are electrical insulators, but become semiconducting when charges are either injected from appropriate electrodes, upon doping or by photoexcitation.
In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor and a Michael acceptor to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.
The Robinson annulation is a chemical reaction used in organic chemistry for ring formation. It was discovered by Robert Robinson in 1935 as a method to create a six membered ring by forming three new carbon–carbon bonds. The method uses a ketone and a methyl vinyl ketone to form an α,β-unsaturated ketone in a cyclohexane ring by a Michael addition followed by an aldol condensation. This procedure is one of the key methods to form fused ring systems.
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.
The Prato reaction is a particular example of the well-known 1,3-dipolar cycloaddition of azomethine ylides to olefins. In fullerene chemistry this reaction refers to the functionalization of fullerenes and nanotubes. The amino acid sarcosine reacts with paraformaldehyde when heated at reflux in toluene to an ylide which reacts with a double bond in a 6,6 ring position in a fullerene via a 1,3-dipolar cycloaddition to yield a N-methylpyrrolidine derivative or pyrrolidinofullerene or pyrrolidino[[3,4:1,2]] [60]fullerene in 82% yield based on C60 conversion.
Hybrid solar cells combine advantages of both organic and inorganic semiconductors. Hybrid photovoltaics have organic materials that consist of conjugated polymers that absorb light as the donor and transport holes. Inorganic materials in hybrid cells are used as the acceptor and electron transporter in the structure. The hybrid photovoltaic devices have a potential for not only low-cost by roll-to-roll processing but also for scalable solar power conversion.
The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.
Triphenylmethanol is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.
Organic photovoltaic devices (OPVs) are fabricated from thin films of organic semiconductors, such as polymers and small-molecule compounds, and are typically on the order of 100 nm thick. Because polymer based OPVs can be made using a coating process such as spin coating or inkjet printing, they are an attractive option for inexpensively covering large areas as well as flexible plastic surfaces. A promising low cost alternative to conventional solar cells made of crystalline silicon, there is a large amount of research being dedicated throughout industry and academia towards developing OPVs and increasing their power conversion efficiency.
An organic solar cell (OSC) or plastic solar cell is a type of photovoltaic that uses organic electronics, a branch of electronics that deals with conductive organic polymers or small organic molecules, for light absorption and charge transport to produce electricity from sunlight by the photovoltaic effect. Most organic photovoltaic cells are polymer solar cells.
Polyfluorene is a polymer with formula (C13H8)n, consisting of fluorene units linked in a linear chain — specifically, at carbon atoms 2 and 7 in the standard fluorene numbering. It can also be described as a chain of benzene rings linked in para positions with an extra methylene bridge connecting every pair of rings.
Photoconductive atomic force microscopy (PC-AFM) is a variant of atomic force microscopy that measures photoconductivity in addition to surface forces.
The Buchner ring expansion is a two-step organic C-C bond forming reaction used to access 7-membered rings. The first step involves formation of a carbene from ethyl diazoacetate, which cyclopropanates an aromatic ring. The ring expansion occurs in the second step, with an electrocyclic reaction opening the cyclopropane ring to form the 7-membered ring.
Polymer-fullerene bulk heterojunction solar cells are a type of solar cell researched in academic laboratories. Photovoltaic cells featuring a polymeric blend of organics have shown promise in a field largely dominated by inorganic solar cells. Specifically, fullerene derivatives act as electron acceptors for donor materials like P3HT, creating a polymer-fullerene based photovoltaic cell.
Diketopyrrolopyrroles (DPPs) are organic dyes and pigments based on the heterocyclic dilactam 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, widely used in optoelectronics. DPPs were initially used as pigments in the painting industry due to their high resistance to photodegradation. More recently, DPP derivatives have been also investigated as promising fluorescent dyes for bioimaging applications, as well as components of materials for use in organic electronics.
Contorted aromatics or more precisely contorted polycyclic aromatic hydrocarbons are polycyclic aromatic hydrocarbons (PAHs) in which the fused aromatic molecules deviate from the usual planarity.
Samson Ally Jenekhe is the Boeing-Martin Professor of Chemical Engineering and Professor of Chemistry at the University of Washington. Jenekhe was previously a chemical engineer at the University of Rochester where his work focused on semiconducting polymers and quantum wires. He has authored over 300 research articles and 28 patents.
Non-fullerene acceptors (NFAs) are types of acceptors used in organic solar cells (OSCs). The name Fullerene comes from another type of acceptor-molecule which was used as the main acceptor material for bulk heterojunction Organic solar cells. Non-fullerene acceptors are thus defined as not being a part of this sort of acceptors.
André Taylor is an American scientist who is an Associate Professor of Chemical Engineering at the New York University Tandon School of Engineering. Taylor works on novel materials for energy conversion and storage. He was awarded the Presidential Early Career Award for Scientists and Engineers in 2010, and named as one of The Community of Scholars' Most Influential Black Researchers of 2020.