195602-17-6

Basic information

• Product Name: 2,3-DIHYDRO-5-(2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXIN-5-YL)THIENO[3,4-B][1,4]DIOXINE
• Synonyms: 2,3-DIHYDRO-5-(2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXIN-5-YL)THIENO[3,4-B][1,4]DIOXINE;2,3-Dihydro-5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thieno[3,4-b]dioxine;5,5'-Bithieno[3,4-b]-1,4-dioxin, 2,2',3,3'-tetrahydro-;2,2',3,3'-tetrahydro-5,5'-bithieno[3,4-b][1,4]dioxine;5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine;2,2',3,3'-tetrahydro-5,5'-Bithieno[3,4-b]-1,4-dioxin
• CAS NO: 195602-17-6
• Molecular Formula: C₁₂H₁₀O₄S₂
• Molecular Weight: 282.34
• Mol File: 195602-17-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 204-205 °C
• Boiling Point: 440 °C at 760 mmHg
• Flash Point: 219.9 °C
• Appearance: /
• Density: 1.474 g/cm³
• Vapor Pressure: 1.57E-07mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,3-DIHYDRO-5-(2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXIN-5-YL)THIENO[3,4-B][1,4]DIOXINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-5-(2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXIN-5-YL)THIENO[3,4-B][1,4]DIOXINE(195602-17-6)
• EPA Substance Registry System: 2,3-DIHYDRO-5-(2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXIN-5-YL)THIENO[3,4-B][1,4]DIOXINE(195602-17-6)

Safety Data

• Hazardous Substances Data: 195602-17-6(Hazardous Substances Data)

Usage

General Description

2,3-Dihydro-5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thieno[3,4-b][1,4]dioxine is a chemical compound belonging to the class of organic compounds known as thienodioxins. Thienodioxins are compounds containing a thieno[3,4-b][1,4]dioxin skeleton, which is structurally characterized by a thiene (an unbranched, acyclic, saturated, or unsaturated aliphatic hydrocarbon having one ring) ring fused to a dioxin (a six-member heterocyclic compound with two oxygen atoms in the ring) ring. Its structure showcases the complexity of organic chemistry as it possesses dioxin rings fused to thiene rings, making it highly specialized and specific. However, specific details regarding its properties, usage, or toxicity are either not well-studied or publicly accessible.

InChI:InChI=1/C12H10O4S2/c1-3-15-9-7(13-1)5-17-11(9)12-10-8(6-18-12)14-2-4-16-10/h5-6H,1-4H2

Upstream product

• 126213-50-1 3,4-(ethylenedioxy)thiophene 
• 302554-82-1 5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxine 
• 862681-10-5 5-(tributyltin)-2,2′-bis(3,4-ethylenedioxy)thiophene 
• 125143-53-5 3,3',5,5'-tetrabromo-2,2'-bithiophene 
• 1020737-20-5 5,5′,5″,5?-tetrabromo-2,3′:2′,2″:3″,2?-quaterthiophene 
• 219621-78-0 5-iodo-2,3-dihydrothieno[3,4-b][1,4]dioxine 

Downstream Products

• 287924-56-5 6,6′-dibromo-4,4′-bithieno[3,4-d][1,3]dioxole 
• 250726-95-5 5,5'-bis(tributylstannyl)-2,2'-bis(3,4-ethylenedioxythiophene) 
• 862681-10-5 5-(tributyltin)-2,2′-bis(3,4-ethylenedioxy)thiophene 
• 1350699-18-1 2-(4-aminophenyl)-3,4,3',4'-bis(ethylenedioxy)-5,2'-bithiophene 
• 1350699-21-6 2-(4-aminophenyl)-3,4,3',4',3,4-ter(ethylenedioxy)-5,2',5',2-terthiophene 
• 1350699-17-0 2-(4-nitrophenyl)-3,4,3',4',3,4-ter(ethylenedioxy)-5,2',5',2-terthiophene 
• 1350699-14-7 5-(4-nitrophenyl)-3,4,3',4'-bis(ethylenedioxy)-[2,2'-bithiophene] 
• 1421943-98-7 4'-(4-(3,4,3',4'-diethylenedioxy-2,5'-bithiophen-5-yl)phenyl)-2,2':6',2''-terpyridine 
• 1015788-42-7 4,4'-(2,2',3,3'-tetrahydro-5,5'-bithieno[3,4-b][1,4]dioxine-7,7'-diyl)bis(N,N-diphenylaniline) 
• 1313877-87-0 7,7'-bis(4-(trifluoromethyl)phenyl)-2,2',3,3'-tetrahydro-5,5'-bithieno[3,4-b][1,4]dioxine 
• 1313877-88-1 diethyl 4,4'-(2,2',3,3'-tetrahydro-5,5'-bithieno[3,4-b][1,4]dioxine-7,7'-diyl)dibenzoate 
• 1301817-70-8 C₃₆H₄₂O₈S₂ 
• 1160930-68-6 7-(4-bromophenyl)-2,2',3,3'-tetrahydro-5,5'-bithieno[3,4-b][1,4]dioxine 
• 336608-05-0 5-formyl-5'-[(E)-(4-N,N-dimethylaminobenzylidene)methyl]-2,2'-bis(3,4-ethylenedioxythiophene) 

Relevant articles and documents

Functionalizafion of 3,4-ethylenedioxythiophene

Syntheses of 3,4-ethylenedioxythiophene-based vinylenes and oligomers are reported.

Modification of the Poly(bisdodecylquaterthiophene) Structure for High and Predominantly Nonionic Conductivity with Matched Dopants

Four p-type polymers were synthesized by modifying poly(bisdodecylquaterthiophene) (PQT12) to increase oxidizability by p-dopants. A sulfur atom is inserted between the thiophene rings and dodecyl chains, and/or 3,4-ethylenedioxy groups are appended to thiophene rings of PQT12. Doped with NOBF4, PQTS12 (with sulfur in side chains) shows a conductivity of 350 S cm-1, the highest reported nonionic conductivity among films made from dopant-polymer solutions. Doped with tetrafluorotetracyanoquinodimethane (F4TCNQ), PDTDE12 (with 3,4-ethylenedioxy groups on thiophene rings) shows a conductivity of 140 S cm-1. The converse combinations of polymer and dopant and formulations using a polymer with both the sulfur and ethylenedioxy modifications showed lower conductivities. The conductivities are stable in air without extrinsic ion contributions associated with PEDOT:PSS that cannot support sustained current or thermoelectric voltage. Efficient charge transfer, tighter ?€-?€ stacking, and strong intermolecular coupling are responsible for the conductivity. Values of nontransient Seebeck coefficient and conductivity agree with empirical modeling for materials with these levels of pure hole conductivity; the power factor compares favorably with prior p-type polymers made by the alternative process of immersion of polymer films into dopant solutions. Models and conductivities point to significant mobility increases induced by dopants on the order of 1-5 cm2 V-1 s-1, supported by field-effect transistor studies of slightly doped samples. The thermal conductivities were in the range of 0.2-0.5 W m-1 K-1, typical for conductive polymers. The results point to further enhancements that could be obtained by increasing doped polymer mobilities.

Strong π-electron donors based on a self-rigidified 2,2′-bi(3,4-ethylenedioxy)thiophene-tetrathiafulvalene hybrid π-conjugated system

Strong π-donors based on the association of TTF and 2,2′-bi(3,4-ethylenedioxy)thiophene conjugating unit have been synthesised; optical and an X-ray data show that intramolecular interactions lead to full rigidification of the conjugated system.

Probing the nature of donor-acceptor effects in conjugated materials: A joint experimental and computational study of model conjugated oligomers

A series of model oligomers consisting of combinations of a traditional strong donor unit (3,4-ethylenedioxythiophene), a traditional strong acceptor unit (benzo[c][1,2,5]thiadiazole), and the ambipolar unit thieno[3,4-b]pyrazine were synthesized via cross-coupling methods. The prepared oligomers include all six possible dimeric combinations in order to characterize the extent and nature of donor-acceptor effects commonly used in the design of conjugated materials, with particular focus on understanding how the inclusion of ambipolar units influences donor-acceptor frameworks. The full oligomeric series was thoroughly investigated via photophysical and electrochemical studies, in parallel with density functional theory (DFT) calculations, in order to correlate the nature and extent of donor-acceptor effects on both frontier orbital energies and the desired narrowing of the HOMO-LUMO energy gap. The corresponding relationships revealed should then provide a deeper understanding of donor-acceptor interactions and their application to conjugated materials.

PYRIDYL-ETHYLENEDIOXY-THIOPHENE DERIVATIVES AS TRANSPARENT CONDUCTIVE MATERIAL

Described herein is a molecule for use as a conductive coating, the molecule comprising pH neutral or substantially neutral functionalities and presenting chemical diversity, transparency in the UV-Vis spectrum and solubility in common organic solvents. Also described herein is film prepared from a solution of a molecule described herein, a method of tuning the properties of a molecule described herein, a transparent electrode and an organic electronic device comprising a molecule described herein.

Preparation of conjugated dimer and products formed therefrom

An improved process for forming a conjugated thiophene precursor is described as in the formation of an improved polymer prepared from the conjugated thiophene and an improved capacitor formed from the improved polymer. The improved process includes forming a thiophene mixture comprising thiophene monomer, unconjugated thiophene oligomer, optionally a solvent and heating the thiophene mixture at a temperature of at least 100° C. to no more than the lower of 250° C. or the boiling point of a component of said thiophene mixture with the lowest boiling point temperature.