145483-63-2

Usage

Uses

Used in Organic Synthesis:
2,5-Bis(tributylstannyl)thiophene is used as a versatile building block for the synthesis of complex organic molecules with specific electronic and optical properties. Its ability to undergo various chemical reactions, such as coupling and cross-coupling reactions, makes it a valuable precursor in this field.
Used in Materials Science:
In the materials science industry, 2,5-Bis(tributylstannyl)thiophene is utilized for the production of organic electronic materials, including conductive polymers and organic semiconductors. Its unique properties and reactivity contribute to the development of advanced materials with potential applications in electronic devices and systems.
Used in Organic Electronics:
2,5-Bis(tributylstannyl)thiophene is employed as a key component in the field of organic electronics, where it plays a crucial role in the fabrication of electronic devices with improved performance and functionality. Its incorporation into organic semiconductors and conductive polymers enhances their electronic properties, making them suitable for various applications in the electronics industry.

Upstream product

• 625-88-7 2,5-diiodothiophene 
• 1461-22-9 tributyltin chloride 
• 188290-36-0 thiophene 
• 3141-27-3 2,5-dibromothiophen 
• 56-35-9 bis(tri-n-butyltin)oxide 

Downstream Products

• 70010-47-8 2,5-bis(4-nitrophenyl)thiophene 
• 193903-62-7 4,4′-(thiophene-2,5-diyl)dibenzaldehyde 
• 1616869-03-4 C₄₈H₄₂N₂O₂S 
• 1616869-02-3 C₃₆H₃₂N₂O₄S 
• 1616869-01-2 C₃₆H₃₃NO₂S 
• 1235583-37-5 DFAG-OT₃-GAFD 
• 55368-38-2 4,4'-(thiophene-2,5-diyl)dibenzonitrile 

Relevant academic research and scientific papers

Synthesis of chromophoric crown-containing styryl derivative of terthiophene and its complexation with octane-1,8-diaminium diperchlorate

2,2′: 5′,2′-Terthiophene derivative containing benzo-18-crown-6 fragments linked through ethene spacers was synthesized, and its complexation with octane-1,8-diaminium diperchlorate in acetonitrile was studied by spectrophotometric titration, 1

Synthesis and organic field effect transistor properties of isoindigo/DPP-based polymers containing a thermolabile group

(E)-6,6′-Dibromo-1,1-bis(2-octyldodecyl)-(3,3′-biindolinylid-ene)-2,2′-dione and/or 2,5-bis(2-octyldodecyl)-3,6-di(5-bromothien-2-yl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione and their tBoc-counterparts were propagated with 2,5-bis(tributylstannyl)thiophene in a molar ratio of 0.8?:?0.2?:?1.0 to release P(ODIDT-BID), P(ODIDT·BDPP), P(ODDPPT·BID) and P(ODDPPT·BDPP) as a new series of random conjugated polymers (RCPs) bearing a large number of octyldodecyl chains to ensure solubility and a small number of thermocleavable tBoc function to cast H-bonding upon heating up to 220 °C. All new polymers were synthesised via Pd catalysed Stille cross-coupling methodology in high yields and reasonable average molecular weights. The cast polymer films exhibited considerable red-shifted UV-vis absorption spectra and a further red-shift was also obtained in the thermal annealed films (at 220 °C for 30 min), which reflected the increasing of crystalline structure. The formation of H-bonding in these polymers was investigated using X-ray diffractometry (XRD) measurements. The field-effect mobilities of these polymers were investigated in the configuration of bottom-gate and bottom-contact (BGBC) field-effect transistors (FETs). The results from FETs indicated that the crystalline structure of RCPs exhibited reasonable FET mobilities with 1.17 × 10?3 cm2 V?1 s?1 for P(ODDPPT·BID) and 1.41 × 10?3 cm2 V?1 s?1 for P(ODDPPT·BDPP).

Donor-acceptor copolymers containing the phthalazinone-thiophene structure synthesized by classical nucleophilic aromatic polymerization

A series of new donor-acceptor copolymers based on a novel monomer containing phthalazinone and thiophene structures, were synthesized by classical nucleophilic displacement step polymerization reaction, and then were fully characterized. Their thermal, optical, electrochemical properties and quantum chemical calculations were investigated in detail. The comparisons between the linkage of ketone/di-ketone/sulfone groups and phenyl/naphthalene groups in the resulting polymer backbone were carried out to explore the relationship of the structure and the properties in the polymer system. The number average molecular weights of the resulting copolymers are 15 kDa-24 kDa. All of the copolymers are stable up to 441 °C, and their 5% weight loss temperatures are higher than 489°C. Their optical band gap and HOMO energy levels vary from 2.36 eV to 2.76 eV and -5.16 eV to -5.51 eV, respectively. The soluble copolymers obtained exhibit blue-fluorescence. Their photoluminescence quantum yield ranges from 0.04 to 0.28 in N-methyl-2-pyrrolidone. These non-ether bond polymers may be potential candidates in photoelectric application.

METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND

PROBLEM TO BE SOLVED: To provide a method for quantitatively producing a group 14 metal lithium compound under a mild condition. SOLUTION: The method for producing a group 14 metal lithium compound represented by formula (4): R4-nMLin comprises reacting a compound represented by formula (1): R4-nMXn and lithium in the presence of a polycyclic aromatic compound represented by formula (2) or formula (3). [In formula (1) and formula (2), R is a hydrocarbon group; M is a metal atom selected from Si, Ge and Sn; X is a halogen atom or R3M- (R and M are the same as mentioned above); and n is 1 or 2] and [R1 is H or a hydrocarbon group; and m is an integer of 0 to 5.] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Stannyl-Lithium: A Facile and Efficient Synthesis Facilitating Further Applications

We have developed a highly efficient, practical, polycyclic aromatic hydrocarbon (PAH)-catalyzed synthesis of stannyl lithium (Sn-Li), in which the tin resource (stannyl chloride or distannyl) is rapidly and quantitatively transformed into Sn-Li reagent at room temperature without formation of any (toxic) byproducts. The resulting Sn-Li reagent can be stored at ambient temperature for months and shows high reactivity toward various substrates, with quantitative atom efficiency.

Linearly π-conjugated oligothiophenes as simple metal-free sensitizers for dye-sensitized solar cells

Four linear oligothiophenes containing 4, 5 and 7 thiophene rings substituted by a variable number of octyl chains attached at the beta-position of some of the thiophene rings and possessing a terminal cyanoacrylic acid anchoring group have been synthesized. Results of UV-Vis absorption spectroscopy and cyclic voltammetry show that as expected the extension of the π-conjugated system leads to a decrease of the optical gap with an increase of the HOMO level. The four compounds have been evaluated as sensitizers in dye-sensitized solar cells (DSSCs) using a iodide/triiodide liquid electrolyte and the results are discussed in terms of the structure-property relationship with regard to the extension of the conjugated system and the number and position of the octyl side chains using N719 as the reference system. A power conversion efficiency of ～7.30% corresponding to 90% of the value given by N719 under identical conditions has been obtained with one of the heptamers.

Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions

This paper reports a study of the synthesis of aryltri-n-butylstannanes via a sonochemical Barbier reaction of aryl- and heteroaryl bromides with bis(tri-n-butyltin) oxide (2) in THF. Our results demonstrate that, despite previous reports on contrary, the aryltributylstannanes can also be obtained under the same reaction conditions via sonicated reactions between aryl monobromides and tri-nbutyltin chloride (2). A comparative study of the reactions of electrophiles 2 and 3 with bromobenzene, 2-bromopyridin, o- and m-bromoanisole, m-bromotoluene, 9-bromophenthrene, and 9-bromoanthracene, indicates that the corresponding aryl- and heteroaryl-tri-n-butylstannyl derivatives are obtained in about the sameyields. Best reaction conditions and the results obtained in the investigation of the sonicated reactions between several aromatic and heteroaromatic dibromides are also reported. It was found that the reactions using 1,2-, 1,3-, and 1,4-dibromobenzenes, 4,40-dibromobiphenyl, 1,4-dibromonaphthalene, 2,5-and 3,5-dibromopyridines, and 2,5-dibromothiophene lead to the corresponding bis(tri-n-butylstannylated) derivatives in many cases in very high yields. Also the excellent results obtained in the sonicated reactions of 1,3,5-tribromobenzene with 2 and 3 are reported.

OLIGOTHIOPHENES DERIVATIVES

The present invention is directed to new oligothiophene derivatives and their use as a semiconductor material in electronic devices. More specifically, the present invention relates to new 3,4-dicyanooligothiophenes derivatives, processes for manufacturing thereof, and to their use as organic n-type (electron-transporting) semiconductors, in particular, in field-effect transistors (FET).