Names | |
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Preferred IUPAC name 2,3-Dihydrothieno[3,4-b][1,4]dioxine | |
Identifiers | |
3D model (JSmol) | |
7126466 | |
ChemSpider | |
ECHA InfoCard | 100.122.178 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H6O2S | |
Molar mass | 142.17 g·mol−1 |
Appearance | colorless liquid |
Density | 1.34 g/cm3 [1] |
Melting point | 10.5 °C (50.9 °F; 283.6 K) [1] |
Boiling point | 225 °C (437 °F; 498 K) [1] |
2.1 g/L [1] | |
Viscosity | 11 mPa·s [1] |
Hazards | |
GHS labelling: [2] | |
Danger | |
H302, H311, H312, H319, H412 | |
P262, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P316, P317, P321, P330, P337+P317, P361+P364, P362+P364, P405, P501 | |
Flash point | 104 °C (219 °F; 377 K) [1] |
360 °C (680 °F; 633 K) [1] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
3,4-Ethylenedioxythiophene (EDOT) is an organosulfur compound with the formula C2H4O2C4H2S. The molecule consists of thiophene, substituted at the 3 and 4 positions with an ethylene glycolyl unit. It is a colorless viscous liquid. [3]
EDOT is the precursor to the polymer PEDOT, which is found in electrochromic displays, photovoltaics, electroluminescent displays, printed wiring, and sensors. [4] [5]
The original synthesis proceeded via the diester of 3,4-dihydroxythiophene-2,5-dicarboxylate.
EDOT is often prepared from C4 precursors such as butanediol and butadiene via routes that produce the thiophene and dioxane rings in separate steps. Representative is the reaction of 2,3-butanedione, trimethyl orthoformate, and ethylene glycol to form the dioxane. Sulfidization with elemental sulfur gives the bicyclic target. [6]
EDOT is converted into the conducting polymer PEDOT by oxidation. The mechanism for this conversion begins with production of the radical cation [EDOT]+, which attacks a neutral EDOT molecule followed by deprotonation. Further similar steps result in the dehydropolymerization. The idealized conversion using peroxydisulfate is shown
For commercial purposes, the polymerization is conducted in the presence of polystyrenesulfonate. [5]
In polymer chemistry, polymerization, or polymerisation, is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many forms of polymerization and different systems exist to categorize them.
Molecular electronics is the study and application of molecular building blocks for the fabrication of electronic components. It is an interdisciplinary area that spans physics, chemistry, and materials science. The unifying feature is use of molecular building blocks to fabricate electronic components. Due to the prospect of size reduction in electronics offered by molecular-level control of properties, molecular electronics has generated much excitement. It provides a potential means to extend Moore's Law beyond the foreseen limits of small-scale conventional silicon integrated circuits.
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O), selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.
Conductive polymers or, more precisely, intrinsically conducting polymers (ICPs) are organic polymers that conduct electricity. Such compounds may have metallic conductivity or can be semiconductors. The main advantage of conductive polymers is that they are easy to process, mainly by dispersion. Conductive polymers are generally not thermoplastics, i.e., they are not thermoformable. But, like insulating polymers, they are organic materials. They can offer high electrical conductivity but do not show similar mechanical properties to other commercially available polymers. The electrical properties can be fine-tuned using the methods of organic synthesis and by advanced dispersion techniques.
Polythiophenes (PTs) are polymerized thiophenes, a sulfur heterocycle. The parent PT is an insoluble colored solid with the formula (C4H2S)n. The rings are linked through the 2- and 5-positions. Poly(alkylthiophene)s have alkyl substituents at the 3- or 4-position(s). They are also colored solids, but tend to be soluble in organic solvents.
Polypyrrole (PPy) is an organic polymer obtained by oxidative polymerization of pyrrole. It is a solid with the formula H(C4H2NH)nH. It is an intrinsically conducting polymer, used in electronics, optical, biological and medical fields.
Polyaniline (PANI) is a conducting polymer and organic semiconductor of the semi-flexible rod polymer family. The compound has been of interest since the 1980s because of its electrical conductivity and mechanical properties. Polyaniline is one of the most studied conducting polymers.
poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT:PSS) is a polymer mixture of two ionomers. One component in this mixture is made up of polystyrene sulfonate which is a sulfonated polystyrene. Part of the sulfonyl groups are deprotonated and carry a negative charge. The other component poly(3,4-ethylenedioxythiophene) (PEDOT) is a conjugated polymer and carries positive charges and is based on polythiophene. Together the charged macromolecules form a macromolecular salt.
Poly(3,4-ethylenedioxythiophene) is a conducting polymer based on 3,4-ethylenedioxythiophene or EDOT. It was first reported by Bayer AG in 1989.
A glucan is a polysaccharide derived from D-glucose, linked by glycosidic bonds. Glucans are noted in two forms: alpha glucans and beta glucans. Many beta-glucans are medically important. They represent a drug target for antifungal medications of the echinocandin class.
Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is a white, odorless, crystalline, indefinitely storable solid, which dissolves in water and many organic solvents. The compound is used as a source of butadiene.
Photothermal therapy (PTT) refers to efforts to use electromagnetic radiation for the treatment of various medical conditions, including cancer. This approach is an extension of photodynamic therapy, in which a photosensitizer is excited with specific band light. This activation brings the sensitizer to an excited state where it then releases vibrational energy (heat), which is what kills the targeted cells.
Poly(3,4-ethylenedioxythiophene)-tetramethacrylate or PEDOT-TMA is a p-type conducting polymer based on 3,4-ethylenedioxylthiophene or the EDOT monomer. It is a modification of the PEDOT structure. Advantages of this polymer relative to PEDOT are that it is dispersible in organic solvents, and it is non-corrosive. PEDOT-TMA was developed under a contract with the National Science Foundation, and it was first announced publicly on April 12, 2004. The trade name for PEDOT-TMA is Oligotron. PEDOT-TMA was featured in an article entitled "Next Stretch for Plastic Electronics" that appeared in Scientific American in 2004. The U.S. Patent office issued a patent protecting PEDOT-TMA on April 22, 2008.
Poly(acrylic acid) (PAA; trade name Carbomer) is a polymer with the formula (CH2-CHCO2H)n. It is a derivative of acrylic acid (CH2=CHCO2H). In addition to the homopolymers, a variety of copolymers and crosslinked polymers, and partially deprotonated derivatives thereof are known and of commercial value. In a water solution at neutral pH, PAA is an anionic polymer, i.e., many of the side chains of PAA lose their protons and acquire a negative charge. Partially or wholly deprotonated PAAs are polyelectrolytes, with the ability to absorb and retain water and swell to many times their original volume. These properties – acid-base and water-attracting – are the bases of many applications.
Transparent conducting films (TCFs) are thin films of optically transparent and electrically conductive material. They are an important component in a number of electronic devices including liquid-crystal displays, OLEDs, touchscreens and photovoltaics. While indium tin oxide (ITO) is the most widely used, alternatives include wider-spectrum transparent conductive oxides (TCOs), conductive polymers, metal grids and random metallic networks, carbon nanotubes (CNT), graphene, nanowire meshes and ultra thin metal films.
Pseudocapacitors store electrical energy faradaically by electron charge transfer between electrode and electrolyte. This is accomplished through electrosorption, reduction-oxidation reactions, and intercalation processes, termed pseudocapacitance.
A polymer capacitor, or more accurately a polymer electrolytic capacitor, is an electrolytic capacitor (e-cap) with a solid conductive polymer electrolyte. There are four different types:
As with any material implanted in the body, it is important to minimize or eliminate foreign body response and maximize effectual integration. Neural implants have the potential to increase the quality of life for patients with such disabilities as Alzheimer's, Parkinson's, epilepsy, depression, and migraines. With the complexity of interfaces between a neural implant and brain tissue, adverse reactions such as fibrous tissue encapsulation that hinder the functionality, occur. Surface modifications to these implants can help improve the tissue-implant interface, increasing the lifetime and effectiveness of the implant.
Conducting redox polymers (CRPs) or intrinsically conducting redox polymers are organic polymers that combine the properties of conducting polymers and redox active polymers. They consist of a conducting polymer backbone with redox active pendant groups.
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