54663-78-4

Usage

Uses

Used in Chemical Synthesis:
2-(TRIBUTYLSTANNYL)THIOPHENE is used as a reactant in the Stille reaction for efficient carbon-carbon bond formation. This reaction is a widely used method in organic chemistry for the formation of carbon-carbon bonds, particularly in the synthesis of complex organic molecules.
Used in Electrochromism Polymers:
2-(TRIBUTYLSTANNYL)THIOPHENE is used as a reactant in the synthesis of diphenylquinoxaline monomer, which is an essential component in the development of electrochromism polymers. These polymers have the ability to change their color and optical properties when an electric current is applied, making them useful in various applications such as smart windows, displays, and optical devices.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-(TRIBUTYLSTANNYL)THIOPHENE could potentially be used in the pharmaceutical industry as a building block for the synthesis of complex organic molecules with therapeutic properties. Its reactivity in the Stille reaction and its ability to form carbon-carbon bonds make it a valuable compound for the development of new drugs and pharmaceutical agents.

InChI:InChI=1/C4H3S.3C4H9.Sn/c1-2-4-5-3-1;3*1-3-4-2;/h1-3H;3*1,3-4H2,2H3;/rC16H30SSn/c1-4-7-13-18(14-8-5-2,15-9-6-3)16-11-10-12-17-16/h10-12H,4-9,13-15H2,1-3H3

Upstream product

• 3437-95-4 2-Iodothiophene 
• 813-19-4 bis(tri-n-butyltin) 
• 1461-22-9 tributyltin chloride 
• 188290-36-0 thiophene 
• 1003-09-4 2-bromothiophene 
• 1067-52-3 tributyltin methoxide 
• 3141-27-3 2,5-dibromothiophen 

Downstream Products

• 492-97-7 2,2'-Bithiophene 
• 1081-34-1 2,2':5',2''-terthiophene 
• 75634-04-7 2-chloro-4-(p-methoxyphenyl)pyrimidine 
• 3779-27-9 2,2'-bithiophene-5-carboxaldehyde 
• 29886-65-5 4-thiophen-2-yl-phenol 
• 16939-09-6 2-naphthalen-2-yl-thiophene 
• 205170-72-5 3’,4’-dinitro-2,2’:5’,2’’-terthiophene 
• 17595-84-5 o-(2-thienyl)benzoic acid methyl ester 
• 130490-48-1 2-benzyl-4-(2-thienyl)-1,2,6-thiadiazine 1,1-dioxide 
• 36242-69-0 (6R,7R)-8-Oxo-7-phenylacetylamino-3-thiophen-2-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 127235-41-0 C₂₉H₂₆N₂O₇S 
• 141753-72-2 C₄₉H₅₈O₂S₄Si₃ 
• 34243-33-9 2-thiophen-2-yl-quinoline 
• 15022-18-1 1-(thiophen-2-yl)propan-2-one 

Relevant academic research and scientific papers

Synthesis and characterization of donor-acceptor type conducting polymers containing benzotriazole acceptor and benzodithiophene donor or: S -indacenodithiophene donor

Two novel electrochromic copolymers, poly(benzodithiophene-benzotriazole) (PBDBT) and poly(s-indacenodithiophene-benzotriazole) (PIDBT) were synthesized successfully through Stille coupling reactions. Both polymers were characterized by cyclic voltammetry

Redox-Active Peptide-Functionalized Quinquethiophene-Based Electrochromic π-Gel

An electrochromic system based on a self-assembled dipeptide-appended redox-active quinquethiophene π-gel is reported. The designed peptide-quinquethiophene consists of a symmetric bolaamphiphile that has two segments: a redox-active π-conjugated quinquethiophene core for electrochromism, and peptide motif for the involvement of molecular self-assembly. Investigations reveal that self-assembly and electrochromic properties of the π-gel are strongly dependent on the relative orientation of peptidic and quinquethiophene scaffolds in the self-assembly system. The colors of the π-gel film are very stable with fast and controlled switching speed at room temperature.

Synthesis of a benzotriazole bearing alternating copolymer for organic photovoltaic applications

A low band gap donor-acceptor (D-A) copolymer PTBTBDT, namely, poly(2-dodecyl-4,7-di(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole-alt-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]dithiophene), was designed and synthesized via a Pd-catalyzed Stille polycondensation reaction. The polymer was characterized using 1H NMR spectroscopy, UV-vis absorption spectroscopy, cyclic voltammetry, and gel permeation chromatography (GPC). PTBTBDT has good solubility in common organic solvents, good thermal stability, broad absorption, low band gap and exhibits not only high hole mobility but also moderate photovoltaic properties. PTBTBDT displays broad absorption in the wavelength range from 300 nm to 630 nm, and its HOMO and LUMO energy levels were calculated to be -4.98 eV and -3.34 eV, respectively. Bulk heterojunction solar cells were fabricated using PTBTBDT as the electron donor and PC70BM as the acceptor. The device exhibits a power conversion efficiency of 2.12% with a current density of 5.45 mA cm-2, an open-circuit voltage of 0.72 V, and a fill factor of 54% under the illumination of AM 1.5 G, 100 mW cm-2. Under similar device fabrication conditions, the PTBTBDT based device showed considerably improved efficiency among its previously synthesized counterparts, i.e. PBDTDTBTz and PBDTBTz based devices, which have 1.7% and 1.4% efficiencies, respectively. The hole mobility of the PTBTBDT: PC70BM (1:2 w/w) blend reached up to 1.47 × 10-3 cm2 V-1 s-1 as calculated by the space-charge-limited current (SCLC) method. By side-chain engineering, this study demonstrates a good example of tuning the absorption range, energy level, charge transport, and photovoltaic properties of polymers.

Fused structures in the polymer backbone to investigate the photovoltaic and electrochromic properties of donor-acceptor-type conjugated polymers

In this study, two new benzotriazole (BTz) and dithienothiophene (DTT) containing conjugated polymers were synthesized. After successful characterizations of the monomers by proton-nuclear magnetic resonance ( 1H NMR) and carbon-NMR (13C NMR) techniques, poly(4-(dithieno[3, 2-b:2′,3′-d]thiophen-2-yl)-2-(2-octyldodecyl)- 2H-benzo[d][1,2,3] triazole) P1 and poly(4-(5-(dithieno[3,2-b:2′,3′- d]thiophen-2-yl)thiophen-2-yl)-2-(2-octyldodecyl)-7-(thiophen-2-yl)-2H-benzo[d] [1,2,3]triazole) P2 were synthesized via a typical Stille coupling. Electrochemical and spectroelectrochemical studies showed that both polymers can be multipurpose materials and used in electrochromic and photovoltaic applications. Reported study indicated that incorporation of DTT into the structure leads to fast switching times compared with BTz-based polymers and competent percentage transmittance in the near-infrared region. Multichromism is important in the context of low-cost flexible display device technology and both polymers are ambipolar and processable as well as multichromic. Throughout the preliminary photovoltaic studies, the best performances of photovoltaic devices were found as Voc = 0.49 V, Jsc = 0.83 mA/cm 2, fill factor (FF) = 34.4%, and power conversion efficiency (PCE) = 0.14% for P1, and as Voc = 0.35 V, Jsc = 1.57 mA/cm 2, FF = 38.2%, and PCE = 0.21% for P2. 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 Benzotriazole- and dithienothiophene-based conjugated polymers were synthesized via Stille coupling. Electrochemical and optical properties of the polymers indicated that the polymers can be great candidates for photovoltaic and electrochromic applications. Therefore, spectroelectrochemical, cyclic voltammetry, and preliminary photovoltaic studies are performed and the results of the studies are highlighted. Copyright

Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.

Electrochromic properties of pyrene conductive polymers modified by chemical polymerization

Pyrene is composed of four benzene rings and has a unique planar melting ring structure. Pyrene is the smallest condensed polycyclic aromatic hydrocarbon, and its unique structural properties have been extensively studied. Pyrene has excellent properties such as thermal stability, high fluorescence quantum efficiency and high carrier mobility. This paper mainly used thiophene, EDOT and triphenylamine groups to enhance the pyrene based π-conjugated system and control the molecular accumulation of organic semiconductors, and improve their charge transport performances. Five kinds of polymer were synthesized and correspondingly characterized. The five kinds of pyrene conductive polymer had outstanding properties in terms of solubility, fluorescence intensity and thermal stability, good film-forming properties, stable electrochromic properties and high coloring efficiency. The coloration efficiency (CE) of PPYTP was as high as 277 cm2C?1, and the switching response time was short. The coloring time of PPYEDOT was 1.3 s and the bleaching time was 3.2 s. The lower impedance will also provide the possibility of such polymers being incorporated into electrochromic devices in the future. In short, the synthesized new pyrene conductive polymers will have wide application prospects in the field of electrochromic materials.

Two-Dimensional Halide Perovskite Materials

The present disclosure relates to novel two-dimensional halide perovskite materials, and the method of making and using the two-dimensional halide perovskite materials.

A facile synthesis of mesoporous graphitic carbon nitride supported palladium nanoparticles as highly effective and reusable catalysts for Stille coupling reactions under mild conditions

The development of a Stille coupling protocol that is operable under moderate conditions without using a base is highly required for the synthetic organic chemistry community, which requires an efficient nanocatalyst. In this respect, addressed herein is a facile one-pot synthesis of mesoporous graphitic carbon nitride (mpg-CN) supported Pd NPs, denoted as mpg-CN/Pd hereafter, and investigation of their catalytic activity in Stille cross-coupling reactions for the first time. It has been demonstrated that mpg-CN nanosheets can serve as not only a support material but also a stabilizer for the generation of 4.5 nm Pd NPs. The ecofriendly generated heterogeneous nanocatalyst was characterized by TEM, XRD, XPS, BET surface area and ICP-MS analysis. The mpg-CN/Pd nanocatalysts showed high activity in the Stille coupling reaction of a variety of electron-deficient and electron-rich aryl iodides/bromides and two different organostannanes with a wide substrate scope to afford the corresponding biaryls without using any bases and additional ligands under relatively mild conditions. The catalyst can be easily recovered from the reaction medium by centrifugation. It can be reused at least 5 times without any loss of activity.

Indole derivative-thiophene compound as well as preparation and application thereof

The invention provides an indole derivative-thiophene compound as well as preparation and application thereof; the compound takes an indole derivative as a central core and thiophene as a peripheral group, and the structure of the compound is shown as a formula (1). The indole derivative-thiophene compound has the main beneficial effects that (1), the indole derivative-thiophene compound has a reticular space structure and is subjected to electrochemical polymerization to form a film, so that the obtained film has a relatively large specific surface area and also has good electrochemical properties such as electrochromism and the like; and (2), a film prepared by electrochemically taking the compound as a monomer can be randomly switched from yellow to green, the optical contrast ratio is20-50%, the response time is 0.5-9s, and the film shows relatively good spectral electrochemical stability in any wave band and is a potential electrochromic material capable of being used for military camouflage.

THIOPHENE MONOAMINE BASED ORGANIC-INORGANIC HYBRID PEROVSKITES

The present disclosure relates to novel thiophene monoamine based organic-inorganic hybrid perovskites, and the method of making and using the novel organic-inorganic hybrid perovskites.