1822-66-8

Usage

Uses

Used in Polymer Industry:
3,4-Dihydroxythiophene-2,5-dicarboxylic acid diethyl ester is used as an intermediate for the synthesis of alkylenedioxythiophene monomers, which are essential in the production of electrochromic conducting polymers. These polymers have various applications, including smart windows, displays, and energy-efficient devices, due to their ability to change color and transmittance in response to an applied voltage.
Used in Electronic Industry:
The electrochromic conducting polymers obtained from 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester have potential applications in the electronic industry, particularly in the development of flexible displays, sensors, and energy storage devices. Their unique properties, such as tunable optical and electronic properties, make them suitable for various electronic applications.
Used in Energy Efficiency Applications:
3,4-Dihydroxythiophene-2,5-dicarboxylic acid diethyl ester contributes to the development of electrochromic conducting polymers that can be used in energy-efficient applications, such as smart windows for buildings and vehicles. These smart windows can dynamically control the amount of sunlight entering a space, reducing the need for artificial lighting and air conditioning, thus saving energy and reducing greenhouse gas emissions.

InChI:InChI=1/C10H12O6S/c1-3-15-9(13)7-5(11)6(12)8(17-7)10(14)16-4-2/h11-12H,3-4H2,1-2H3

Upstream product

• 14282-56-5 diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate disodium salt 
• 925-47-3 diethyl thioglycolate 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 177364-92-0 diethyl 3,4-dimethoxythiophene-2,5-dicarboxylate 
• 79764-90-2 3,4-diacetoxy-thiophene-2,5-dicarboxylic acid diethyl ester 
• 79765-87-0 3,4-bis-benzoyloxy-thiophene-2,5-dicarboxylic acid diethyl ester 
• 177364-96-4 3,4-dimethoxythiophene-2,5-dicarboxylic acid 
• 14282-58-7 3,4-dihydroxy-2,5-dicarboxylic acid thiophene 
• 122372-64-9 16,18-bis(ethoxycarbonyl)-2,5,8,11,14-pentaoxa-17-thiabicyclo<13.3.0>octadeca-1(18),15-diene 
• 122372-67-2 22,24-bis(ethoxycarbonyl)-2,5,8,11,14,17,20-heptaoxa-23-thiabicyclo<19.3.0>tetracosa-1(24),21-diene 
• 122372-66-1 19,21-bis(ethoxycarbonyl)-2,5,8,11,14,17-hexaoxa-20-thiabicyclo<16.3.0>heneicosa-1(21),18-diene 
• 154934-13-1 2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester 
• 122372-62-7 13,15-bis(ethoxycarbonyl)-2,5,8,11-tetraoxa-14-thiabicyclo<10.3.0>pentadeca-1(15),12-diene 
• 122372-63-8 13,15,28,30-tetrakis(ethoxycarbonyl)-2,5,8,11,17,20,23,26-octaoxa-14,29-dithiatricyclo<25.3.0.0^12,16>triaconta-1(30),12,15,27-tetraene 
• 177364-93-1 3,4-Dibutoxy-thiophene-2,5-dicarboxylic acid diethyl ester 
• 153846-91-4 3,4-Bis-decyloxy-thiophene-2,5-dicarboxylic acid diethyl ester 
• 177364-95-3 diethyl 3,4-bis(benzyloxy)thiophene-2,5-dicarboxylate 

Relevant academic research and scientific papers

Aminothiophene sulfonic acid ester

PROBLEM TO BE SOLVED: To provide 3,4-disubstituted thiophene sulfonate usable as a monomer for a conductive polymer, and not having carboxylate on 2,5-positions, and to provide a method for producing the same.SOLUTION: This thiophene sulfonate is represented by general formula (1). The thiophene sulfonate is obtained, for example, by decarboxylation of 3,4-dihydroxy-2,5-dicarboxylic acid thiophene in a basic inert solvent, followed by reaction with sulfonyl chlorides in the presence of a tertiary alkylamine catalyst. (In the formula, Rand Reach independently represent a 1-8C alkyl, phenyl or tolyl).

Preparation of an EDOT-based polymer: Optoelectronic properties and electrochromic device application

Here we present the synthesis, characterization and electropolymerization of a new EDOT-based monomer; 5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine (DTD). Electrochemical polymerization of DTD was performed potentiostatically by using dichloromethane (DCM) as solvent and tetrabutylammonium hexafluorophosphate (TBPF6) as supporting electrolyte. Homopolymer [P(DTD)] films and copolymer [P(DTD-co-TPA)] films of DTD prepared by using 4-(2,5-di(thiophen-2-yl)-1H-pyrrole-1-yl)butane-1-amine (TPA) were characterized via CV and UV-vis spectroscopy. Spectroelectrochemical analysis of P(DTD) revealed electronic transitions at 585 nm (π-π transition) with an electronic band gap of 1.69 eV. Electrochromic studies revealed that P(DTD) has competitive properties to EDOT. Furthermore, a dual-type complementary colored polymer electrochromic device based on P(DTD) and P(TPA) was constructed in sandwich configuration. Spectroelectrochemical studies revealed that the oxidized state of the device shows a blue color whereas it is yellow in the reduced state. The maximum contrast (Δ%T) and switching time of the device were measured as 25.5% and 0.5 s for 385 nm and 21% and 1.0 s for 550 nm.

Photo tuning of thiophene-2,5-dicarbohydrazide derivatives for their photoalignment ability-molecular modelling studies

In this work, we reported a photoalignment of a nematic liquid crystal, promoted by thin alignment layers made from novel thiophene-2,5-dicarbohydrazide derivatives after being illuminated with linear polarized UV light. A clear indication of the relationship between the molecular structure and alignment properties of the materials was obtained by introducing a methyl substituent group (-CH3) in the molecular structure of some of the materials studied in this work. Interestingly, the illumination with linear polarized UV caused the preferred direction of liquid crystal alignment, promoted by these layers, to be oriented either parallel (in the case of the thiophene derivative without methyl substitution) or perpendicular (in the case of the thiophene derivative with methyl substitution). The mechanism behind the observed alignment effect is elucidated by molecular modelling studies. These studies suggested the change of the orientation of the molecular net dipole moment, when a methyl group is incorporated in the molecular structure of the materials, as a possible origin. Such information is indispensable for the design and synthesis of novel photo-alignment materials for liquid crystal displays of high quality.

Preparation method of 3,4-ethylenedioxythiophene

A method of preparing 3,4-ethylenedioxythiophene is provided. The preparation is performed by microwave heating to greatly increase the yield and decrease the reaction time, energy consumption, solvent usage, and environmental damage.

Synthesis and anticonvulsant activity of some new bishydrazones derived from 3,4-dipropyloxythiophene

A series of new 3,4-dipropyloxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides (4-30) were synthesized from ethyl thiodiglycolate and diethyloxalate through multistep reactions. Following Dieckmann-Komppa reaction, the required precursor 3,4-dihydroxythiophene-2,5-diester (1) was prepared. This was derivatized with propyl bromide and further converted to corresponding hydrazide (3), which was finally transformed to targeted hydrazones (4-30) by conventional methods. The newly synthesized compounds were characterized using FT-IR, 1H and 13C NMR, EI-MS and elemental analyses. The anticonvulsant activity of all the title compounds was investigated against maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scMET) models and their neurotoxicity was also evaluated. Some of the selected compounds were subjected to 6 Hz test in order to evaluate their uncover activities. Compound 3,4-dipropyloxy-N2,N5-bis[1-(2-thienyl)ethylidene]thiophene-2,5-dicarbohydrazide (15) has emerged as a lead in this series with less neurotoxicity.

A new class of anticonvulsants possessing 6 Hz activity: 3,4-Dialkyloxy thiophene bishydrazones

Thirty nine new 3,4-di(substituted)oxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides were synthesized starting from ethyl thiodiglycolate through multi-step reactions. In the synthetic sequence, 3,4-dihydroxythiophene-2,5-diester (1) was obtained by condensing the ethyl thiodiglycolate with diethyl oxalate. It was derivatized using different alkyl halides to give disubstituted thiophene esters (2-5), which were then converted to corresponding hydrazides (6-9) following usual methods. Finally, these hydrazides, on treatment with various substituted carbonyl compounds underwent smooth condensation to yield target hydrazones (10-13). The new compounds were characterized using FT-IR, 1H NMR and 13C NMR, mass spectral and elemental analyses. The anticonvulsant activity of the title compounds was established after intraperitoneal (ip) administration in three seizure models, which include maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) and 6 Hz screens and their neurotoxicity was also evaluated. Compound 11f has emerged as an active compound with no neurotoxicity in this series. Also, the structure-activity relationship of the tested compounds was discussed.

Prussian blue nanoparticles protected by the water-soluble π-conjugated polymer PEDOT-S: Synthesis and multiple-color pH-sensing with a redox reaction

Prussian blue nanoparticles (PB NPs), stabilized for the first time by the π-conjugated polymer poly(4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2yl-methoxy- 1-butanesulfonic acid, potassium salt) (PEDOT-S), demonstrated a novel multiple-color pH-sensing function with a redox reaction based on the electronic interaction between the PB nano-core and the PEDOT-S shell. The Royal Society of Chemistry 2009.

CARBOXYLIC ACID-MODIFIED EDOT FOR BIOCONJUGATION

An electroconductive carboxylic acid functionalized monomer corresponding to Formula (I), wherein A represents a hydrogen or a carboxyl group. Polymerized monomers of Formula (I) conjugated with a biomolecule result in conjugated PEDOT polymers of Formula (III) wherein A is a hydrogen or a carboxylic acid group and B is a biomolecule selected from the group consisting of a peptide, a protein, a lipid, a carbohydrate and a polynucleotide. The biomolecule conjugated polymers can be disposed onto an electrically conductive substrate wherein the substrate has a first layer of PEDOT polymerized on a surface of the substrate and a second layer of biomolecule conjugated PEDOT polymer of Formula (III) polymerized on the first layer of PEDOT. The first and second layers form a charge transport material in electrical communication with the conductive substrate. The electrically conductive substrate further comprises a dopant.

DERIVATIZED 3,4-ALKYLENEDIOXYTHIOPHENE MONOMERS, METHODS OF MAKING THEM, AND USE THEREOF

The present invention relates to methods of making derivatized 3,4-alkylenedioxythiophene monomers and methods of using the 3,4-alkylenedioxythiophene monomers.

The first direct experimental comparison between the hugely contrasting properties of PEDOT and the all-sulfur analogue PEDTT by analogy with well-defined EDTT-EDOT copolymers

The structures of poly(3,4-ethylenedioxythiophene) (PEDOT) and poly(3,4-ethylenedithiathiophene) (PEDTT) vary only in the substituent chalcogen atoms, yet the electronic properties of the materials are surprisingly dissimilar. The difference in electronic band gaps is approximately 0.8 eV and the polymers behave very differently upon p-doping. Two new terthiophenes have been synthesised using Negishi coupling methods. The X-ray crystal structures of EDOT-EDTT-EDOT (OSO) and EDTT-EDOT-EDTT (SOS) show strong intramolecular chalcogen-chalcogen contacts which are responsible for persistent conformers in solution and solid state, although significant interchain interactions should also influence the properties of the materials. SOS and OSO can be polymerised by electrochemical oxidation to give the corresponding, well-defined poly(terthiophenes) PSOS and POSO. Spectroelectrochemical studies on all four polymers reveal strong similarities between PEDTT and PSOS, and between PEDOT and POSO. Together with independent electrochemical and absorption studies, the results indicate that the unique properties of PEDOT are influenced more by conformational effects (intrachain S...O contacts) than substituent effects. The Royal Society of Chemistry 2005.