175922-79-9

Usage

Uses

Used in Organic Synthesis:
Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane is utilized as a reagent in organic synthesis for the formation of carbon-carbon and carbon-heteroatom bonds. Its ability to facilitate these bond formations is crucial for the synthesis of complex organic molecules.
Used in Polymer Production:
In the polymer industry, Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane is employed in the production of polymers. Its role in this process is to aid in the formation of polymer chains, contributing to the development of materials with specific properties.
Used as a Stabilizer in Plastics Manufacturing:
Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane also serves as a stabilizer in the manufacturing of plastics. It helps to prevent the degradation of plastic materials, thereby extending their lifespan and maintaining their structural integrity.
Environmental and Health Considerations:
Despite its applications, Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane has been identified as toxic to marine organisms. This has led to restrictions on its use due to the potential environmental and health hazards associated with organotin compounds. As a result, the chemical industry is actively seeking alternative compounds that can perform similar functions without the associated risks.

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 
• 1159894-38-8 2-[4-[N,N-bis-(4-hexyloxyphenyl)amino]phenyl]-3,4-(ethylenedioxy)thiophene 
• 1192035-52-1 4-(3,4-(ethylenedioxy)thiophen-2-yl)-N,N-bis(4-((2-ethylhexyl)oxy)phenyl)anline 
• 1383942-32-2 C₄₄H₄₅NO₆S₄ 
• 1383942-49-1 C₄₅H₄₅NO₅S₄ 
• 1383942-53-7 C₄₄H₄₇NO₅S₃ 
• 1383942-56-0 C₄₈H₄₆N₂O₆S₄ 
• 1384897-25-9 4-[5-(3,4-ethylenedioxy)thienyl]-N,N-bis(4-methoxyphenyl)aniline 
• 1449334-15-9 4-methoxy-N-(4-methoxyphenyl)-N-(4-(7-(tributylstannyl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)phenyl)aniline 
• 1449334-22-8 C₅₇H₆₁NO₇S₃ 
• 1449334-19-3 C₆₀H₆₂N₂O₈S₃ 
• 1417779-55-5 4-(3,4-ethylenedioxythiophen-2-yl)-N,N-bis(4-methylphenyl)aniline 
• 1417779-70-4 5-(7-(5-(4-(N,N-bis(4-((2-ethylhexyl)oxy)phenyl)amino)pheny)-3,4-(ethylenedioxy)thiophen-2-yl)-9-oxo-9H-fluoren-2-yl)thiophene-2-carbaldehyde 

Relevant academic research and scientific papers

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.

Yellow-to-blue switching of indole[3,2-b]carbazole-based electrochromic polymers and the corresponding electrochromic devices with outstanding photopic contrast, fast switching speed, and satisfactory cycling stability

Three novel π-conjugated indolo[3,2-b]carbazole derivatives, 2,8-di(thiophen-2-yl)-5,11-dioctyl-indolo[3,2-b] carbazole (TICZ), 2,8-bis(4-ethylthiophen-2-yl)-5,11-dioctyl-indolo[3,2-b]carbazole (ETICZ) and 2,8-bis(2-(3,4-ethylenedioxythiophene))-5,11-dioctyl-indolo[3,2-b]carbazole (EDTICZ), were synthesized and electrochemically polymerized to afford the corresponding polymers. The effects of different substituent groups on thiophen units in terms of optical, electrochemical, and electrochromic properties and the performance of electrochromic devices (ECDs) were investigated in detail. Electrochemical and optical analysis demonstrated that incorporation of strong auxochromic groups resulted in polymer PEDTICZ with low oxidation potentials, red-shifted absorption peaks and corresponding narrow band gap values but is unfavorable for incorporating ethyl groups. Spectroelectrochemical studies indicated an evident variation in the absorption spectra as well as significant color changes for all of the polymer films upon application of an external potential. PTICZ had high optical contrast with visible light (58.6%), fast switching speed (0.92 s), and satisfactory coloration efficiency (167 cm2 C?1). Of these three systems, the results for PEDTICZ were next best, and those for PETICZ were third. Also, there was a larger contrast (82.7% and 57.8%) in the NIR region (1500 nm) for the PTICZ and PEDTICZ films, respectively. Along with high coloring efficiencies, these results indicate that these systems are favorable for many NIR applications.

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.

Synthesis and optical properties of some 3,4-(ethylenedioxythiophen-2-yl)-1,2,4-triazine derivatives

A series of a hybrid oligomers with different combinations of thiophene, EDOT and 1,2,4-triazine rings have been synthesized and characterized. The synthesis of these alternated 1,2,4-triazine derivatives is reported using a straightforward palladium mediated Stille coupling reaction of 2-tri-n-butyltin-3,4-ethylenedioxythiophene with 3-methylsulfanyl-1,2,4-triazine. The molecular structure and the potential optoelectronic properties of the newly obtained compounds were characterized by UV–Vis absorption and emission spectra, X-ray analysis and theoretical calculations at the DFT level.

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.

Evidence for the contribution of sulfur-bromine intramolecular interactions to the self-rigidification of thiophene-based π-conjugated systems

Bithiophene associating 3,4-ethylenedioxythiophene and 3-bromothiophene, and the corresponding polymer exhibit self-rigidified structures of the conjugated backbones resulting from the association of S-Br and S-O non-bonded intramolecular interactions. Th

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.

Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor-acceptor-donor type polymers

A new benzimidazole unit, 4′-(tert-butyl)spiro[benzo[d]imidazole-2, 1′-cyclohexane] was synthesized and coupled with different donor units like 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT) via Stille coupling. The donor-acceptor-donor (D-A-D) ty

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.

Tuning band structures of dyes for dye-sensitized solar cells: Effect of different π-bridges on the performance of cells

Three organic dyes (LJ101, LJ102, and LJ103) with different π-bridges such as thiophene, 3-hexylthiophene and 3, 4-ethyldioxythiophene, were prepared and applied for the dye-sensitized solar cells (DSSCs). The effect of the different π-bridges on the phot