175922-79-9

Basic information

• Product Name: Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane
• Synonyms: Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane;Tributyl(3,4-ethylenedioxythienyl-2)stannane;Tributyl[3,4-(ethylenedioxy)-2-thienyl]tin;3,4-Ethylenedioxy-2-(tributylstannyl)thiophene
• CAS NO: 175922-79-9
• Molecular Formula: C₁₈H₃₂O₂SSn
• Molecular Weight: 431.22048
• EINECS: 200-258-5
• Mol File: 175922-79-9.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 434.4±55.0 °C(Predicted)
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane(CAS DataBase Reference)
• NIST Chemistry Reference: Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane(175922-79-9)
• EPA Substance Registry System: Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane(175922-79-9)

Safety Data

• Hazardous Substances Data: 175922-79-9(Hazardous Substances Data)

Usage

General Description

Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane is an organotin compound that contains a central tin atom bonded to four butyl groups and a thieno-dioxin-yl group. Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane is used in organic synthesis as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds. It is also used in the production of polymers and as a stabilizer in the manufacturing of plastics. However, organotin compounds like tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane have been found to be toxic to marine organisms and have been subject to restrictions in their use due to their potential environmental and health hazards.

Upstream product

• 109-72-8 n-butyllithium 
• 1461-22-9 tributyltin chloride 
• 126213-50-1 3,4-(ethylenedioxy)thiophene 
• 1461-22-9 tri-n-butylstannyl chloride 

Downstream Products

• 300806-18-2 5?(4?nitrophenyl)?2,3?dihydrothieno[3,4?b][1,4]dioxine 
• 1068163-09-6 (3',4'-ethylenedioxy-2',5-bithiophene)(diphenyl)phosphine oxide 
• 1001078-63-2 (4-bromo-phenyl)-bis[4-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)phenyl]amine 
• 1001078-64-3 bis(4-bromophenyl)-[4-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)phenyl]amine 
• 1159894-38-8 2-[4-[N,N-bis-(4-hexyloxyphenyl)amino]phenyl]-3,4-(ethylenedioxy)thiophene 
• 1383942-32-2 C₄₄H₄₅NO₆S₄ 
• 1383942-49-1 C₄₅H₄₅NO₅S₄ 
• 1383942-53-7 C₄₄H₄₇NO₅S₃ 
• 1383942-56-0 C₄₈H₄₆N₂O₆S₄ 
• 1138217-20-5 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-bis(2,3-dihydrothieno[3,4-b][1,4]-dioxin-5-yl)quinoxaline 
• 1001330-07-9 3,8-bis(3,4-(ethylenedioxy)thien-2-yl)-1,10-phenanthroline 
• 925674-61-9 2-(2-pyridyl)-3,4-ethylenedioxythiophene 
• 944998-35-0 2-(3-pyridyl)-3,4-ethylenedioxythiophene 

Relevant articles and documents

Electropolymerized three-dimensional randomly branched edot-containing copolymers

The potential of 2,2′;3,2″-terthiophene (3T) as branching units in 3D copolymers is presented with EDOT as an example comonomer. Branched EDOT/3T polythiophenes were prepared by electropolymerization, and their electrochemical and optical properties are discussed. Two different approaches were employed: (i) the direct electropolymerization of a novel branched thiophene monomer (3TE3) consisting of a 3T core that contains three outer EDOT end groups and (ii) the electrochemical copolymerization of a EDOT/3T mixture in different ratios from [1:1] to [1:10]. Cyclic voltammetric and vis spectrometric experiments show that the EDOT content within the polymer has a strong influence on the electronic properties of the material: with increasing EDOT content, the HOMO-LUMO gap is decreased. To prove copolymer formation of EDOT and 3T, chemically synthesized reference copolymers of EDOT and 3T were prepared by oxidative coupling using FeCl3, and their optical and electronic properties were compared to those of the electrodeposited films. In addition, the copolymer formation is indicated by the comparison of the electrochemical and spectroscopic results with those of the homopolymers P3T and PEDOT.

Structure and photocatalytic activity of a low band gap donor-acceptor-donor (D-A-D) type conjugated polymer: poly(EDOT-pyridazine-EDOT)

A donor-acceptor-donor (D-A-D) type monomer (3,6-bis(2-(3,4-ethylenedioxy thiophene))pyridazine, EPE) with pyridazine as an intermediate unit (acceptor) and 3,4-ethylenedioxythiophene (EDOT) as a sealing unit (donor) was prepared. The monomer was then polymerized by adjusting various ratios of FeCl3/monomer to prepare a donor-acceptor-donor (D-A-D) type conjugated polymer: poly(EPE). The results from a structural analysis indicated that the conjugation length, doping level, thermal stability, crystallinity, as well as the morphologies of the poly(EPE)s can be affected by the oxidant?:?monomer ratio. The resulting products were characterized by 1H NMR, FT-IR, UV-vis, TGA, XRD, EDX and SEM. Studies were carried out on the photocatalytic performance of the poly(EPE)s for the photocatalytic degradation of different dyes (methylene blue (MB), methyl violet (MU), methyl orange (MO), rhodamine B (RhB) and phenol) (5 mg L?1) under xenon-lamp irradiation, and the same type of light source and different catalysts (poly(EPE)s and PEDOT) on the degradation efficiency of MU were investigated, which showed that poly(EPE) was an effective photocatalyst, and the presence of Fe ions in the polymer matrix played a significant role in enhancing the photocatalytic activity of poly(EPE). Among the poly(EPE)s, the doped poly(EPE)2 ([FeCl3]/[EPE] ratio of 8?:?1) achieved the highest degradation efficiency (95.53%) for MU dye under the simulation of a visible light source for 300 min.

A Free-standing electrochromic material of poly(5,7-bis(2-(3,4-ethylenedioxy)thienyl)-indole) and its application in electrochromic device

Free-standing poly(5,7-bis(2-(3,4-ethylenedioxy)thienyl)-indole) (PETI) was electrochemically obtained from 5,7-bis(2-(3,4-ethylenedioxy)thienyl)-indole (ETI) prepared by Stille coupling reaction of 5,7-dibromoindole and 3,4-ethylenedioxythiophene. For comparison, poly(5,7-bis(2-thiophene)-indole) was also electrosynthesized from 5,7-bis(2-thiophene)-indole (BTI) which was prepared from the 5,7-dibromoindole and thiophene. Characterizations of ETI and BTI were performed by cyclic voltammetry, scanning electron microscopy, 1H NMR, and 13C NMR spectroscopy. Spectroelectrochemical studies showed PETI had better electrochromic properties and showed two different colors (brown and blue-violet) under various potentials with better maximum contrast (ΔT%) and coloration efficiency (CE). An electrochromic device (ECD) based on PETI and poly(3,4-ethylenedioxythiophene) (PEDOT) was also constructed and characterized. This ECD had fast response time, high CE, better optical memory, and long-term stability. These results indicated that PETI had potential applications for ECD.

Intramolecular charge transfer (ICT) of a chiroptically active conjugated polymer showing green colour

A donor-acceptor type achiral monomer 4,7-bis(2,3-dihydrothieno[3,4-b]-1,4-dioxin-5-yl)-2,1,3-benzothiadiazole was synthesised and electrochemically polymerised in a cholesteric liquid crystalline (CLC) medium. This film exhibits a fingerprint pattern under the polarised optical microscopic observation. A possible mechanism of the fingerprint structure formation through a procedure of electrochemical polymerisation in a CLC medium is presented. The preparation of chiral polymer films even from achiral monomers is demonstrated. The film shows green colour in the reduced state and blue in the oxidised state. Changes in colour and CD signals of the film are repeatable with electrochemical oxidation and reduction. The presence of radical cations in the chiral environment, referred to as chiralions, distributed along chiral polymer chains is proposed.

Highly fluorescent triazolopyridine-thiophene D-A-D oligomers for efficient pH sensing both in solution and in the solid state

Conjugated fluorophores have been extensively used for fluorescence sensing of various substances in the field of life processes and environmental science, due to their noninvasiveness, sensitivity, simplicity and rapidity. Most existing conjugated fluorophores exhibit excellent light-emitting performance in dilute solutions, but their properties substantially decrease or even completely vanish due to severe aggregation quenching in the solid state. Herein, we synthesize a series of triazolopyridine-thiophene donor-acceptor-donor (D-A-D) type conjugated molecules with high absolute fluorescence quantum yields (ΦF) ranging from 80% to 89% in solution. These molecules also show unusual light-emitting properties in the solid state with ΦF of up to 26%. We find that owing to the protonation-deprotonation process of the pyridine ring, these compounds display obvious changes in both fluorescence wavelength and intensity upon addition of acids, and these changes can be readily recovered by the successive introduction of bases. By harnessing this phenomenon, we further show that these fluorophores can be employed for efficient and reversible fluorescence sensing of hydrogen ions in a broad pH range (0.0-7.0). With the fabrication of pH testing papers and ink-printed complex patterns including butterflies and letters on substrates, we demonstrate the application of such sensors to fluorescence indication or solid state pH detection for real samples such as volatile acidic/basic gas and water-quality analysis.

Synthesis, characterization and photovoltaic properties of a low-bandgap platinum(II) polyyne functionalized with a 3,4-ethylenedioxythiophene-benzothiadiazole hybrid spacer

The synthesis, characterization and optical spectroscopy of a deep blue platinum(II) polyyne functionalized with the (3,4-ethylenedioxythiophene)-benzothiadiazole hybrid spacer (P1) and its dinuclear platinum molecular model complex (M1) are described. This metalated polymer P1 exhibits good thermal stability and possesses a narrow bandgap of 1.76 eV. Optical spectroscopic measurements of these materials reveal a substantial donor-acceptor interaction along the rigid backbone of the organometallic polyynes through the interaction of metal center and the conjugated tricyclic ligand. Preliminary study shows that P1: methanofullerene acceptor blend can be used as an active layer of bulk-heterojunction polymer solar cells. Photoexcitation of this blend layer in some yet-to-be optimized cells results in a photo-induced electron transfer from the π-conjugated metallopolyyne electron donor to [6,6]-phenyl C61-butyric acid methyl ester with a power conversion efficiency (PCE) close to 0.30% under air mass (AM1.5) simulated solar illumination. The power dependencies of the solar cell parameters (including the short-circuit current density, open-circuit voltage, fill-factor and PCE) were also studied.

Design of twisted conjugated molecular systems towards stable multi-colored electrochromic polymers

Promising advancement of conjugated polymers in electrochromic devices require to design high-performance electrochromic polymers with rich color conversion and long-term stability under cyclic electrical loads. Here we report a new strategy in developing multi-colored electrochromic polymers with good stability via twisted conjugated molecular engineering. A series of twisted hybrid precursors are synthesized by coupling ortho-alkylenedioxybenzenes with EDOT units, and their corresponding polymers are facilely electrosynthesized at relatively low polymerization potentials. The structure-property relationships of such ortho-alkylenedioxybenzene-EDOT hybrid precursors and polymers are systematically elucidated via DFT calculations, spectral, morphological, electrochemical and spectroelectrochemical analysis, etc. We demonstrate that the dihedral angle between ortho-alkylenedioxybenzenes and EDOT moieties can substantially affect the electrochemical and electrochromic properties of polymers. As the dihedral angle and electron cloud density increases, these hybrid polymers display distinct multiple color switching nature and good overall performance including high coloration efficiency (>200 cm2 C?1), decent optical contrast (>45percent), fast switching (1 s), and excellent switching stability (96percent of optical contrast after 3500 cycling) under cyclic electrical loads. With these findings, this work will provide novel insights for rational design of stable and highly efficient multi-colored electrochromic polymers.

Poly[3,4-ethylene dioxythiophene (EDOT)-co-1,3,5-tri[2-(3,4-ethylene dioxythienyl)]-benzene (EPh)] copolymers (PEDOT-co-EPh): Optical, electrochemical and mechanical properties

PEDOT-co-EPh copolymers with systematic variations in composition were prepared by electrochemical polymerization from mixed monomer solutions in acetonitrile. The EPh monomer is a trifunctional crosslinking agent with three EDOTs around a central benzene ring. With increasing EPh content, the color of the copolymers changed from blue to yellow to red due to decreased absorption in the near infrared (IR) spectrum and increased absorption in the visible spectrum. The surface morphology changed from rough and nanofibrillar to more smooth with rounded bumps. The electrical transport properties dramatically decreased with increasing EPh content, resulting in coatings that either substantially lowered the impedance of the electrode (at the lowest EPh content), leave the impedance nearly unchanged (near 1% EPh), or significantly increase the impedance (at 1% and above). The mechanical properties of the films were substantially improved with EPh content, with the 0.5% EPh films showing an estimated 5× improvement in modulus measured by AFM nanoindentation. The PEDOT-co-EPh copolymer films were all shown to be non-cytotoxic toward and promote the neurite outgrowth of PC12 cells. Given these results, we expect that the films of most interest for neural interface applications will be those with improved mechanical properties that maintain the improved charge transport performance (with 1% EPh and below). This journal is

Thiophene derivative as well as synthesis method and application thereof

The invention discloses a thiophene derivative (E2SBFE2) as shown in a formula 1, 2,7-bis(2,2',3,3'-tetrahydro-5,5'-dithieno[3,4-b][1,4]dioxene)-9,9'-spirobifluorene, a synthetic method of the thiophene derivative and application of the thiophene derivative as a polymer emulsion additive. The E2SBFE2 can be used as an additive to be compounded with a PVDC emulsion to prepare a composite emulsion E2SBFE2-coated PVDC, and the composite emulsion is particularly suitable for being smeared on hard sheets such as PVC and the like to prepare composite hard sheets and has the advantage of high yellowing resistance.

EDOT-quinoxaline-EDOT derivative and preparation method and application thereof

The invention relates to an EDOT-quinoxaline-EDOT derivative, a preparation method of the EDOT-quinoxaline-EDOT derivative and application of an electrochemical polymerized film of the EDOT-quinoxaline-EDOT derivative as a novel photoelectric functional m