5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene

Base Information

• Chemical Name: 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene
• CAS No.: 143367-56-0
• Molecular Formula: C14H22S2Sn2
• Molecular Weight: 491.881
• Mol file: 143367-56-0.mol

Synonyms:5,5-bis(trimethylstannyl)-2,2′-bithiophene;.2,5'-bis(trimethylstannyl)-5-(2'-thienyl)thiophene;.5,5'-bis-(trimethylstannyl)-2,2'-dithiophene;.2,2'-bithiophene-5,5'-bis(trimethylstannane);5,5'-BIS(TRIMETHYLSTANNYL)-2,2'-BITHIOPHENE;.2,5'-bis(trimethylstannyl)-2,2'-bithiophene;5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene;5,5;

Chemical Property of 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene

Chemical Property:

• Melting Point: 96-100°C
• Boiling Point: 418.2±55.0 °C(Predicted)
• PSA: 56.48000
• LogP: 4.56700
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature

Purity/Quality:

98% ^*data from raw suppliers

5,5′-Bis(trimethylstannyl)-2,2′-bithiophene 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+,N
• Statements: 26/27/28-50/53
• Safety Statements: 26-27-28-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Description: 5,5'-bis(trimethylstannyl)-2,2'-bithiophene?can be used for the synthesis of small molecules and polymer semiconductors for OFETs, OLED, PLED, OPV applications.5,5'-bis(trimethylstannyl)-2,2'-bithiophene can be prepared from 2,2'-bithiophene which is an electron rich and donating unit if it is embedded into low band-gap polymer semiconductors.

Technology Process of 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene

There total 5 articles about 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,2'-Bithiophene (492-97-7) + trimethyltin(IV)chloride (1066-45-1) → 5,5'-bis(trimethylstannyl)-2,2'-bithiophene (143367-56-0)

Guidance literature:

2,2'-Bithiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -40 - 25 ℃; for 2h;

trimethyltin(IV)chloride; In tetrahydrofuran; hexane; at -40 - 25 ℃; for 3h;

Reference yield: 80.0%

(trimethylstannyl)lithium (17946-71-3) + 5,5'-dibromo-2,2'-bisthiophene (4805-22-5) → 5,5'-bis(trimethylstannyl)-2,2'-bithiophene (143367-56-0)

Guidance literature:

In tetrahydrofuran; Sn-compd. soln. addn. dropwise to org, compd. soln. at 0°C, stirring overnight at room temp., solvent vac. evapn., residue extn. (n-hexane); solvent evapn., solid recrystn. (hexane); elem. anal.;

Reference yield: 75.0%

5,5'-dibromo-2,2'-bisthiophene (4805-22-5) + trimethyltin(IV)chloride (1066-45-1) → 5,5'-bis(trimethylstannyl)-2,2'-bithiophene (143367-56-0)

Guidance literature:

5,5'-dibromo-2,2'-bisthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

trimethyltin(IV)chloride; In tetrahydrofuran; hexane; at 20 ℃;

DOI:10.1021/ja203189h

upstream raw materials:

2,2'-Bithiophene

trimethyltin(IV)chloride

(trimethylstannyl)lithium

5,5'-dibromo-2,2'-bisthiophene

Downstream raw materials:

5,5'-bis-[bis-(4-tert-butyl-phenyl)-boranyl]-[2,2']bithiophenyl

C₂₈H₂₀N₂S₂

3,3?-didodecyl-2,2′;5′,2″;5″,2?-quaterthiophene

5,5'''-dibromo-3,3'''-bis(dodecyl)-2,2':5',2'':5'',2'''-quarterthiophene

Refernces

A Solution-Processable meso-Phenyl-BODIPY-Based n-Channel Semiconductor with Enhanced Fluorescence Emission

10.1002/cplu.201900317

The research aims to design, synthesize, and characterize a new acceptor-donor-acceptor (AD-A) semiconductor, BDY-Ph-2T-Ph-BDY, which features a central phenyl-bithiophene-phenyl p-donor and BODIPY p-acceptor end-units. The purpose is to develop a solution-processable n-channel semiconductor with enhanced fluorescence emission for next-generation optoelectronics. The study concludes that BDY-Ph-2T-Ph-BDY exhibits an optical band gap of 2.32 eV, highly stabilized HOMO/LUMO energies (-5.74 eV/-3.42 eV), and a D-A dihedral angle of ~66°. It shows good fluorescence efficiency (FF = 0.30) and n-channel OFET transport characteristics (μe = 0.005 cm2/V·s; Ion/Ioff = 104-105), representing a significant improvement in fluorescence quantum yield compared to previous BODIPY semiconductors. This work demonstrates the potential of BDY-Ph-2T-Ph-BDY for high-performance optoelectronic applications. 4-Bromobenzaldehyde is used as a starting material to introduce the phenyl group into the BODIPY structure. N-Ethylpyrrole acts as a building block for the BODIPY core. P-Chloranil (2,3,5,6-Tetrachloro-1,4-benzoquinone) is used as an oxidizing agent in the synthesis process.

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