640737-72-0

Usage

Uses

Used in Polymerization Method Development:
5,7-Diiodo-2,3-dihydrothieno[3,4-b][1,4]dioxine is used as a key compound in the development of a polymerization method for poly(3,4-ethylenedioxythiophene) (PEDOT). The presence of the iodine atoms in the compound allows for the formation of a highly conductive polymer, which is essential for various electronic applications.
Used in Electronics Industry:
In the electronics industry, 5,7-Diiodo-2,3-dihydrothieno[3,4-b][1,4]dioxine is used as a precursor for the synthesis of conductive polymers like PEDOT. These polymers are utilized in the manufacturing of organic electronic devices, such as organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and flexible electronic circuits.
Used in Research and Development:
5,7-Diiodo-2,3-dihydrothieno[3,4-b][1,4]dioxine is also used as a research compound for studying the properties and behavior of conductive polymers. Its unique structure allows scientists to explore new ways to improve the performance and stability of these materials, which can lead to the development of more advanced electronic devices and technologies.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 5,7-Diiodo-2,3-dihydrothieno[3,4-b][1,4]dioxine may also have potential applications in the pharmaceutical industry. Its unique chemical structure could be exploited for the development of new drugs or drug delivery systems, particularly in the areas of neurodegenerative diseases, where conductive polymers have shown promise.

Upstream product

• 126213-50-1 3,4-(ethylenedioxy)thiophene 
• 640737-73-1 2,5-diacetoxymercuro-3,4-ethylenedioxythiophene 

Relevant academic research and scientific papers

Phenothiazine Based Donor–Acceptor Compounds with Solid-State Emission in the Yellow to NIR Region and Their Highly Selective and Sensitive Detection of Cyanide Ion in ppb Level

Four new novel donor–acceptor (A-π-D-A, A-D-π-D-A) compounds (1 a, 1 b, 2 a and 2 b) based on ethylenedioxythiophene (EDOT) and phenothiazine (PTz) have been rationally designed and synthesized towards solid state emission ranging from yellow to near infrared (NIR). The compounds 1 b and 2 b, in thin film form, showed an emission maximum at 713 nm and 696 nm, respectively, with the corresponding absolute solid-state quantum yield of 3.3 % and 9.0 %. The fluorophores showed high emission in the doped state as well when dispersed in polystyrene (PS) matrix with emission maximum ranging from 536 nm to 648 nm with quantum yield in the range 12.4 %–64.4 %. The presence of dicyanovinyl (DCV) group in both the fluorophores was exploited towards cyanide sensing in DMSO leading to turn-on fluorescence emission with high selectivity and sensitivity for cyanide ion with a detection limit of as low as 0.32 μm (8 ppb) for 1 b and 0.57 μm (14 ppb) for 2 b. DFT and TTDFT calculations suggested that the addition of cyanide ion prevented the intramolecular charge transfer (ICT) from the donor (PTz or EDOT) to acceptor (DCV), thereby turning the fluorescence “On”. Using fluorescent spectral and color switching, we have explored logic gates with single and two input signal amplification by applying chemical and light inputs in the form of CN? ion and UV.

Variable band gap poly(arylene ethynylene) conjugated polyelectrolytes

A series of poly(arylene ethynylene) (PAE) conjugated polyelectrolytes (CPEs) have been prepared using palladium-mediated (Sonogashira) coupling chemistry. The series consists of five pairs of polymers that share the same poly(arylene ethynylene) backbone. One member of each pair contains anionic sulfonate (R-SO3-) side groups, whereas the other member contains cationic bis-alkylammonium (R-N+-R-N+-R) side groups. The repeat unit structure of the poly(arylene ethynylene) backbone consists of a bis(alkoxy)phenylene-1,4-ethynylene unit alternating with a second arylene ethynylene moiety, and five different arylenes were used, Ar = 1,4-phenyl, 2,5-pyridyl (Py), 2,5-thienyl (Th), 2,5-(3,4-ethylenedioxy)thienyl (EDOT), and 1,4-benzo[2,1,3]-thiodiazole (BDT). The different arylene units induce variation in the HOMO-LUMO band gap across the series of polymers, resulting in a series of materials that display absorption maxima at wavelengths ranging from 400 to 550 nm and fluorescence maxima ranging from 440 to 600 nm. The absorption and fluorescence properties of the CPEs were investigated in methanol, water, and in methanol/water mixtures. The photophysical data suggest that the CPE chains aggregate in water, but in methanol, the polymers are well solvated such that the optical properties are characteristic of the molecularly dissolved chains. Stem-Volmer (SV) fluorescence quenching studies were carried out using ionic naphthalene diimides as electron acceptors. The results show that the fluorescence from the CPEs was quenched with very high efficiency (amplified quenching) when the ionic diimide was charged opposite to the charge on the CPE chain. The sensitivity of the Stern-Volmer quenching response varies strongly across the series of CPEs, with the most efficient quenching seen for polymers that display efficient fluorescence when they are aggregated. The relationship between CPE side chain structure, band gap, fluorescence quantum yield, extent of chain aggregation, and fluorescence quenching efficiency is discussed.

Highly soluble electroactive ethylenedioxythiopene (EDOT)-based copolymer obtained via ‘click’ copolymerization

Poly (3,4-ethylenedioxythiophene) (PEDOT), in spite of its remarkable attributes, remains insoluble in many common solvents. By adopting the copolymerization approach, a new electroactive polythiopene derivative is synthesized with enhanced solubility by polymerizing an alkyne-functionalized (3-4-ethylenedioxythiophene) (EDOT) and an azide-functionalized tetraethylene glycol via copper catalyzed alkyne-azide cycloaddition (CuAAC). The copolymer, EDOT-co-1,2,3-triazolium, exhibits an interesting chemical structure that makes it an ideal electroactive material. With its polar nature, it readily dissolves in solvents such as DMSO, DMF and PC. Furthermore, the introduction of the oxyethylene monomer as well as the formation of the 1,2,3-triazole during the polymerization step lowers its glass transition temperature inducing a faster switching between its reduced and oxidized state compared to pristine PEDOT.

Compound, preparation method and applications thereof, and organic electrochromic device

The invention discloses a compound, a preparation method and applications thereof, and an organic electrochromic device, wherein the compound has a structural formula represented by the following formula (I) or (II). According to the present invention, according to the compound represented by the formula (I) or (II), 3,4-ethylenedioxythiophene (EDOT) is used as a parent nucleus, nitro naphthalenemethyl ketone is bridged on one side or both sides, and the alpha-H of methyl ketone is relatively active, and can be subjected to reversible and stable enol isomerization under different acid-alkaliconditions, such that the material has excellent electrochromic performance.

Clean and Efficient Iodination of Thiophene Derivatives

Iodination of thiophene derivatives is realized using a simple, fast, and efficient methodology. Iodination of thiophene and 2- or 3-substituted or 3,4-disubstituted thiophenes with N-iodosuccinimide (NIS) activated with 4-toluenesulfonic acid in ethanol gives pure iodinated products that require no further purification.

Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species

In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.

Deprotonative cadmation of functionalized aromatics

This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium-cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases. The Royal Society of Chemistry.

Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented Heterocyclic Coupling Reaction

Prolonged storage (～2 years) or gentle heating (50-80 °C) of crystalline 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) affords a highly conducting, bromine-doped poly(3,4-ethylenedioxythiophene) (PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR spectroscopies. The novel solid-state polymerization (SSP) does not occur for 2,5-dichloro-3,4-ethylenedioxythiophene (DCEDOT), and requires a much higher temperature (>130 °C) for 2,5-diiodo-3,4-ethylenedioxythiophene (DIEDOT). X-ray structural analysis of the above dihalothiophenes reveals short Hal...Hal distances between adjacent molecules in DBEDOT and DIEDOT, but not in DCEDOT. The polymerization may also occur in the melt but is significantly slower and leads to poorly conductive material. Detailed studies of the reaction were performed using ESR, DSC, microscopy, and gravimetric analyses. SSP starts on crystal defect sites; it is exothermic by 14 kcal/mol and requires activation energy of ～26 kcal/mol (for DBEDOT). The temperature dependence of the conductivity of SSP-PEDOT (σrt = 20-80 S/cm) reveals a slight thermal activation. It can be further increased by a factor of 2 by doping with iodine. Using this approach, thin films of PEDOT with conductivity as high as 20 S/cm were fabricated on insulating flexible plastic surfaces.