Names | |
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Preferred IUPAC name 5,12-Dihydroquinolino[2,3-b]acridine-7,14-dione | |
Other names C.I.: 73900, Pigment Violet 19 | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.012.618 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C20H12N2O2 | |
Molar mass | 312.328 g·mol−1 |
Appearance | Red powder (nanoparticles) |
Density | 1.47 g/cm3 |
Insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial colorant applications such as robust outdoor paints, inkjet printer ink, tattoo inks, artists' watercolor paints, and color laser printer toner. As pigments, the quinacridones are insoluble. [1] [2] The development of this family of pigments supplanted the alizarin dyes.[ citation needed ]
The name indicates that the compounds are a fusion of acridone and quinoline, although they are not made that way. Classically the parent is prepared from the 2,5-dianilide of terephthalic acid (C6H2(NHPh)2(CO2H)2). Condensation of succinosuccinate esters with aniline followed by cyclization affords dihydroquinacridone, which are readily dehydrogenated. The latter is oxidized to quinacridone. [1] Derivatives of quinacridone can be readily obtained by employing substituted anilines. Linear cis-Quinacridones can be prepared from isophthalic acid. [3] [4]
Isomers of quinacridone |
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Linear trans-Isomer |
Linear cis-Isomer |
Angular cis-Isomer |
Angular trans-Isomer |
Quinacridone-based pigments are used to make high performance paints. Quinacridones were first sold as pigments by Du Pont in 1958. [5] Quinacridones are considered "high performance" pigments because they have exceptional color and weather fastness. Major uses for quinacridones include automobile and industrial coatings. Nanocrystalline dispersions of quinacridone pigments functionalized with solubilizing surfactants are the most common magenta printing ink.
Typically deep red to violet in color, the hue of quinacridone is affected not only by the R-groups on the molecule but by the crystal form of the solid. For example, the γ crystal modification of unsubstituted quinacridone provides a strong red shade that has excellent color fastness and resistance to solvation. Another important modification is the β phase which provides a maroon shade that is also more weather resistant and light-fast. Both crystal modifications are more thermodynamically stable than the α crystal phase. The γ crystal modification is characterized by a criss-cross lattice where each quinacridone molecule hydrogen-bonds to four neighbors via single H-bonds. The β phase, meanwhile, consists of linear chains of molecules with double H-bonds between each quinacridone molecule and two neighbors. [6]
Basic modifications to the chemical structure of quinacridones include the addition of CH3 and Cl substituents. Some magenta shades of quinacridone are labeled under the proprietary name "Thio Violet" [7] and "Acra Violet". [8]
Quinacridone derivatives exhibit intense fluorescence in the dispersed state, and high carrier mobility. These properties complement good photo-, thermal, and electrochemical stability. These properties are desired for optoelectronic applications including organic light-emitting diodes (OLEDs), organic solar cells (OSCs), and organic field-effect transistors (OFETs). Due to interplay of intermolecular H-bonding and pi-pi stacking, quinacridone can form a self-assembling, supramolecular organic semiconductor.
A set of primary colors or primary colours consists of colorants or colored lights that can be mixed in varying amounts to produce a gamut of colors. This is the essential method used to create the perception of a broad range of colors in, e.g., electronic displays, color printing, and paintings. Perceptions associated with a given combination of primary colors can be predicted by an appropriate mixing model that reflects the physics of how light interacts with physical media, and ultimately the retina. The most common color mixing models are the additive primary colors and the subtractive primary colors. Red, yellow and blue are also commonly taught as primary colours, despite some criticism due to its lack of scientific basis.
Magenta is a purplish-red color. On color wheels of the RGB (additive) and CMY (subtractive) color models, it is located precisely midway between blue and red. It is one of the four colors of ink used in color printing by an inkjet printer, along with yellow, cyan, and black to make all the other colors. The tone of magenta used in printing, printer's magenta, is redder than the magenta of the RGB (additive) model, the former being closer to rose.
A pigment is a powder used to add color or change visual appearance. Pigments are completely or nearly insoluble and chemically unreactive in water or another medium; in contrast, dyes are colored substances which are soluble or go into solution at some stage in their use. Dyes are often organic compounds whereas pigments are often inorganic. Pigments of prehistoric and historic value include ochre, charcoal, and lapis lazuli.
Color theory, or more specifically traditional color theory, is the historical body of knowledge describing the behavior of colors, namely in color mixing, color contrast effects, color harmony, color schemes and color symbolism. Modern color theory is generally referred to as Color science. While there is no clear distinction in scope, traditional color theory tends to be more subjective and have artistic applications, while color science tends to be more objective and have functional applications, such as in chemistry, astronomy or color reproduction. Color theory dates back at least as far as Aristotle's treatise On Colors. A formalization of "color theory" began in the 18th century, initially within a partisan controversy over Isaac Newton's theory of color and the nature of primary colors. By the end of the 19th century, a schism had formed between traditional color theory and color science.
Subtractive color or subtractive color mixing predicts the spectral power distribution of light after it passes through successive layers of partially absorbing media. This idealized model is the essential principle of how dyes and pigments are used in color printing and photography, where the perception of color is elicited after white light passes through microscopic "stacks" of partially absorbing media allowing some wavelengths of light to reach the eye and not others, and also in painting, whether the colors are mixed or applied in successive layers.
Copper phthalocyanine (CuPc), also called phthalocyanine blue, phthalo blue and many other names, is a bright, crystalline, synthetic blue pigment from the group of dyes based on phthalocyanines. Its brilliant blue is frequently used in paints and dyes. It is highly valued for its superior properties such as light fastness, tinting strength, covering power and resistance to the effects of alkalis and acids. It has the appearance of a blue powder, insoluble in most solvents including water.
Supramolecular chemistry refers to the branch of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from weak intermolecular forces, electrostatic charge, or hydrogen bonding to strong covalent bonding, provided that the electronic coupling strength remains small relative to the energy parameters of the component. While traditional chemistry concentrates on the covalent bond, supramolecular chemistry examines the weaker and reversible non-covalent interactions between molecules. These forces include hydrogen bonding, metal coordination, hydrophobic forces, van der Waals forces, pi–pi interactions and electrostatic effects.
In supramolecular chemistry, host–guest chemistry describes complexes that are composed of two or more molecules or ions that are held together in unique structural relationships by forces other than those of full covalent bonds. Host–guest chemistry encompasses the idea of molecular recognition and interactions through non-covalent bonding. Non-covalent bonding is critical in maintaining the 3D structure of large molecules, such as proteins and is involved in many biological processes in which large molecules bind specifically but transiently to one another.
Crystal engineering studies the design and synthesis of solid-state structures with desired properties through deliberate control of intermolecular interactions. It is an interdisciplinary academic field, bridging solid-state and supramolecular chemistry.
Rose madder is a red paint made from the pigment madder lake, a traditional lake pigment extracted from the common madder plant Rubia tinctorum.
Arylide yellow, also known as Hansa yellow and monoazo yellow, is a family of organic compounds used as pigments. They are primarily used as industrial colorants including plastics, building paints and inks. They are also used in artistic oil paints, acrylics and watercolors. These pigments are usually semi-transparent and range from orange-yellow to yellow-greens. Related organic pigments are the diarylide pigments. Overall, these pigments have partially displaced the toxic cadmium yellow in the marketplace. Painters such as Alexander Calder and Jackson Pollock are known to have employed arylide yellow in their artworks.
Michler's ketone is an organic compound with the formula of [(CH3)2NC6H4]2CO. This electron-rich derivative of benzophenone is an intermediate in the production of dyes and pigments, for example Methyl violet. It is also used as a photosensitizer. It is named after the German chemist Wilhelm Michler.
The color magenta has notable tints and shades. These various colors are shown below.
A metalloanthocyanin is a chemical complex giving color to petals of certain plants.
Lightfastness is a property of a colourant such as dye or pigment that describes its resistance to fading when exposed to light. Dyes and pigments are used for example for dyeing of fabrics, plastics or other materials and manufacturing paints or printing inks.
Pigment Violet 29 is an organic compound that is used as a pigment and vat dye. Its colour is dark red purple, or bordeaux.
Paint mixing is the practice of mixing components or colors of paint to combine them into a working material and achieve a desired hue. The components that go into paint mixing depend on the function of the product sought to be produced. For example, a painter of portraits or scenery on a canvas may be seeking delicate hues and subtle gradiations, while the painter of a house may be more concerned with durability and consistency of colors in paints presented to customers, and the painter of a bridge or a ship may have the weatherability of the paint as their primary concern.
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.
Diethylsuccinoylsuccinate is an organic compound with the formula [CH2C(OH)=C(CO2Et)]2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate:
A colorant is any substance that changes the spectral transmittance or reflectance of a material. Synthetic colorants are those created in a laboratory or industrial setting. The production and improvement of colorants was a driver of the early synthetic chemical industry, in fact many of today's largest chemical producers started as dye-works in the late 19th or early 20th centuries, including Bayer AG(1863). Synthetics are extremely attractive for industrial and aesthetic purposes as they have they often achieve higher intensity and color fastness than comparable natural pigments and dyes used since ancient times. Market viable large scale production of dyes occurred nearly simultaneously in the early major producing countries Britain (1857), France (1858), Germany (1858), and Switzerland (1859), and expansion of associated chemical industries followed. The mid-nineteenth century through WWII saw an incredible expansion of the variety and scale of manufacture of synthetic colorants. Synthetic colorants quickly became ubiquitous in everyday life, from clothing to food. This stems from the invention of industrial research and development laboratories in the 1870s, and the new awareness of empirical chemical formulas as targets for synthesis by academic chemists. The dye industry became one of the first instances where directed scientific research lead to new products, and the first where this occurred regularly.