Squaraine Rotaxane
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Squaraine Rotaxane
Squaraine dyes are a class of organic dyes showing intense fluorescence, typically in the red and near infrared region (absorption maxima are found between 630 and 670 nm and their emission maxima are between 650–700 nm). They are characterized by their unique aromatic four membered ring system derived from squaric acid. Most squaraines are wikt:encumbered, encumbered by nucleophilic attack of the central four membered ring, which is highly electron deficient. This encumbrance can be attenuated by the formation of a rotaxane around the dye to protect it from nucleophiles. They are currently used as sensors for ions and have recently, with the advent of protected squaraine derivatives, been exploited in biomedical imaging. Synthesis Synthesis of squaraine dyes was reported at least in 1966. They are derived from squaric acid which undergoes an electrophilic aromatic substitution reaction with an aniline or another electron rich derivative to form a highly conjugated prod ...
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Dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.Rossberg, M. ''et al.'' (2006) "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. . Occurrence Natural sources of dichloromethane include oceanic sources, macroalgae, wetlands, and volcanoes. However, the majority of dichloromethane in the environment is the result of industrial emissions. Production DCM is produced by treating either chloromethane or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and chloromethane undergo a series of reactions producing progressively more chlorinated products. In this way, an estimated 400,000 tons were produced in the US, Europe, and Japan in 1993. ...
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Squaric Acid
Squaric acid, also called quadratic acid because its four carbon atoms approximately form a square, is a diprotic organic acid with the chemical formula C4O2(OH)2. The conjugate base of squaric acid is the hydrogensquarate anion ; and the conjugate base of the hydrogensquarate anion is the divalent squarate anion . This is one of the oxocarbon anions, which consist only of carbon and oxygen. Squaric acid is a reagent for chemical synthesis, used for instance to make photosensitive squaraine dyes and inhibitors of protein tyrosine phosphatases. Chemical properties Squaric acid is a white crystalline powder. The onset of thermal decomposition depends on the different thermodynamic conditions such as heating rates. The structure of squaric acid is not a perfect square, as the carbon–carbon bond lengths are not quite equal. The high acidity with p''K''a = 1.5 for the first proton and p''K''a = 3.4 for the second is attributable to resonance stabilization of the anion. Because t ...
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Raman Scattering
Raman scattering or the Raman effect () is the inelastic scattering of photons by matter, meaning that there is both an exchange of energy and a change in the light's direction. Typically this effect involves vibrational energy being gained by a molecule as incident photons from a visible laser are shifted to lower energy. This is called normal Stokes Raman scattering. The effect is exploited by chemists and physicists to gain information about materials for a variety of purposes by performing various forms of Raman spectroscopy. Many other variants of Raman spectroscopy allow rotational energy to be examined (if gas samples are used) and electronic energy levels may be examined if an X-ray source is used in addition to other possibilities. More complex techniques involving pulsed lasers, multiple laser beams and so on are known. Light has a certain probability of being scattered by a material. When photons are scattered, most of them are elastically scattered (Rayleigh scatt ...
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Luminescence
Luminescence is spontaneous emission of light by a substance not resulting from heat; or "cold light". It is thus a form of cold-body radiation. It can be caused by chemical reactions, electrical energy, subatomic motions or stress on a crystal. This distinguishes luminescence from incandescence, which is light emitted by a substance as a result of heating. Historically, radioactivity was thought of as a form of "radio-luminescence", although it is today considered to be separate since it involves more than electromagnetic radiation. The dials, hands, scales, and signs of aviation and navigational instruments and markings are often coated with luminescent materials in a process known as "luminising". Types The following are types of luminescence: * Chemiluminescence, the emission of light as a result of a chemical reaction **Bioluminescence, a result of biochemical reactions in a living organism **Electrochemiluminescence, a result of an electrochemical reaction **Lyolumine ...
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Optical Properties Of Carbon Nanotubes
The optical properties of carbon nanotubes are highly relevant for materials science. The way those materials interact with electromagnetic radiation is unique in many respects, as evidenced by their peculiar absorption, photoluminescence (fluorescence), and Raman spectra. Carbon nanotubes are unique "one-dimensional" materials, whose hollow fibers (tubes) have a unique and highly ordered atomic and electronic structure, and can be made in a wide range of dimension. The diameter typically varies from 0.4 to 40 nm (i.e., a range of ~100 times). However, the length can reach , implying a length-to-diameter ratio as high as 132,000,000:1; which is unequaled by any other material. Consequently, all the electronic, optical, electrochemical and mechanical properties of the carbon nanotubes are extremely anisotropic (directionally dependent) and tunable. Applications of carbon nanotubes in optics and photonics are still less developed than in other fields. Some properties that ...
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Carbon Nanotubes
A scanning tunneling microscopy image of a single-walled carbon nanotube Rotating single-walled zigzag carbon nanotube A carbon nanotube (CNT) is a tube made of carbon with diameters typically measured in nanometers. ''Single-wall carbon nanotubes'' (''SWCNTs'') are one of the allotropes of carbon, intermediate between fullerene cages and flat graphene, with diameters in the range of a nanometre. Although not made this way, single-wall carbon nanotubes can be idealized as cutouts from a two-dimensional Hexagonal tiling, hexagonal lattice of carbon atoms rolled up along one of the Bravais lattice vectors of the hexagonal lattice to form a hollow cylinder. In this construction, periodic boundary conditions are imposed over the length of this roll-up vector to yield a helical lattice of seamlessly bonded carbon atoms on the cylinder surface. ''Multi-wall carbon nanotubes'' (''MWCNTs'') consisting of nested single-wall carbon nanotubes weakly bound together by van der Waals i ...
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Quantum Yield
The quantum yield (Φ) of a radiation-induced process is the number of times a specific event occurs per photon absorbed by the system. Applications Fluorescence spectroscopy The fluorescence quantum yield is defined as the ratio of the number of photons emitted to the number of photons absorbed.Lakowicz, Joseph R. ''Principles of Fluorescence Spectroscopy'' (Kluwer Academic / Plenum Publishers 1999) p.10. Fluorescence quantum yield is measured on a scale from 0 to 1.0, but is often represented as a percentage. A quantum yield of 1.0 (100%) describes a process where each photon absorbed results in a photon emitted. Substances with the largest quantum yields, such as rhodamines, display the brightest emissions; however, compounds with quantum yields of 0.10 are still considered quite fluorescent. Quantum yield is defined by the fraction of excited state fluorophores that decay through fluorescence: where \Phi_ is the fluorescence quantum yield, k_ is the rate constant f ...
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Squarylium
Squaraine dyes are a class of organic dyes showing intense fluorescence, typically in the red and near infrared region (absorption maxima are found between 630 and 670 nm and their emission maxima are between 650–700 nm). They are characterized by their unique aromatic four membered ring system derived from squaric acid. Most squaraines are encumbered by nucleophilic attack of the central four membered ring, which is highly electron deficient. This encumbrance can be attenuated by the formation of a rotaxane around the dye to protect it from nucleophiles. They are currently used as sensors for ions and have recently, with the advent of protected squaraine derivatives, been exploited in biomedical imaging. Synthesis Synthesis of squaraine dyes was reported at least in 1966. They are derived from squaric acid which undergoes an electrophilic aromatic substitution reaction with an aniline or another electron rich derivative to form a highly conjugated product with extens ...
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Fluorescence
Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation. It is a form of luminescence. In most cases, the emitted light has a longer wavelength, and therefore a lower photon energy, than the absorbed radiation. A perceptible example of fluorescence occurs when the absorbed radiation is in the ultraviolet region of the electromagnetic spectrum (invisible to the human eye), while the emitted light is in the visible region; this gives the fluorescent substance a distinct color that can only be seen when the substance has been exposed to UV light. Fluorescent materials cease to glow nearly immediately when the radiation source stops, unlike phosphorescent materials, which continue to emit light for some time after. Fluorescence has many practical applications, including mineralogy, gemology, medicine, chemical sensors (fluorescence spectroscopy), fluorescent labelling, dyes, biological detectors, cosmic-ray detection, vacu ...
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Aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses aniline Aniline is an organic compound with the formula C6 H5 NH2. Consi .... It is an industrially significant Commodity chemicals, commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It Combustion, ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone ...
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic nitration, aromatic halogenation, aromatic sulfonation, and alkylation and acylation Friedel–Crafts reaction. Illustrative reactions The most widely practised example of this reaction is the ethylation of benzene. :: Approximately 24,700,000 tons were produced in 1999. (After dehydrogenation and polymerization, the commodity plastic polystyrene is produced.) In this process, acids are used as catalyst to generate the incipient carbocation. Many other electrophilic reactions of benzene are conducted, although on a much smaller scale; they are valuable routes to key intermediates. The nitration of benzene is achieved via the action of the nitronium ion as the electrophile. The sulfonation with fuming sulfuric acid gives benzenesulfonic ac ...
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