13130-50-2

Basic information

• Product Name: 2 2':5' 2''-TERTHIOPHENE-5 5''-DICARBOX&
• Synonyms: 2 2':5' 2''-TERTHIOPHENE-5 5''-DICARBOX&;2,2:5,2-Terthiophene-5,5-dicarboxaldehyde;2,2':5',2''-terthiophene-5,5''-dicarbox-aldehyde,;2,2'':5'',2''-TERTHIOPHENE-5,5''-DICARBOXALDEHYDE,98%;5,5''-Diformyl-2,2':5',2''-terthiophene;[2,2':5',2''-terthiophene]-5,5''-dicarbaldehyde;2,2':5',2''-Terthiophen-5,5''-dicarbaldehyde
• CAS NO: 13130-50-2
• Molecular Formula: C₁₄H₈O₂S₃
• Molecular Weight: 304.41
• Mol File: 13130-50-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 218-222 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 2 2':5' 2''-TERTHIOPHENE-5 5''-DICARBOX&(CAS DataBase Reference)
• NIST Chemistry Reference: 2 2':5' 2''-TERTHIOPHENE-5 5''-DICARBOX&(13130-50-2)
• EPA Substance Registry System: 2 2':5' 2''-TERTHIOPHENE-5 5''-DICARBOX&(13130-50-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13130-50-2(Hazardous Substances Data)

Usage

General Description

2,2':5',2''-terthiophene-5,5''-dicarboxylate is a chemical compound that belongs to the family of organic compounds known as thiophenes. It is a derivative of thiophene, which is a five-membered ring containing four carbon atoms and one sulfur atom. 2 2':5' 2''-TERTHIOPHENE-5 5''-DICARBOX& is commonly used in the field of organic electronics, particularly as a building block in the synthesis of organic semiconductor materials. Its unique structure and properties make it a valuable component in the development of various electronic devices such as organic light-emitting diodes, organic solar cells, and organic field-effect transistors. Furthermore, its carboxylate groups allow for easy functionalization, making it a versatile and useful compound in the field of materials chemistry.

Upstream product

• 1081-34-1 2,2':5',2''-terthiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 13669-05-1 1,4-bis(thiophen-2-yl)butane-1,4-dione 
• 110046-60-1 5'-bromo-2,2'-bithiophene-5-carboxaldehyde 
• 3779-27-9 2,2'-bithiophene-5-carboxaldehyde 
• 110046-61-2 (5'-bromo-[2,2'-bithiophen]-5-yl)methanol 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 98057-08-0 5,5'-dibromo-2,2':5'2''-terthiophene 

Downstream Products

• 122510-05-8 5,2''-diformyl-2,2':5',5''-terthiophene di(N,N-diphenylhydrazone) 
• 1050615-26-3 5,2''-diformyl-2,2':5',5''-terthiophene di(N-methyl-N-phenylhydrazone) 

Relevant articles and documents

Precise one-pot synthesis of end-functionalized conjugated multi-block copolymers via combined olefin metathesis and wittig-type coupling

A precise, one-pot synthesis of end-functionalized block copolymers consisting of poly(9,9-di-n-octylfluorene-2,7-vinylene)s (PFVs) and oligo(2,5-dialkoxy-1,4-phenylenevinylene) or terthiophene units as the middle segment have been prepared by olefin metathesis of the vinyl group in the PFV chain ends followed by subsequent Wittig-type coupling. Formation of the block copolymers and the quantitative efficiency in the end-functionalization can be confirmed by synthesis of amphiphilic block copolymers containing poly(ethylene glycol) at the both polymer chain ends. Effect of PFV conjugation length, middle segment, and the end groups toward the emission properties have been studied: the polymers containing ferrocene moiety at the chain ends displayed unique emission/quenching properties.

Efficient synthesis of RITA and its analogues: Derivation of analogues with improved antiproliferative activity via modulation of p53/miR-34a pathway

A novel approach to synthesize RITA by practical palladium-catalyzed C-C bond-forming Suzuki reactions at room temperature was developed, which was used for deriving a series of substituted tricyclic α-heteroaryl (furan/thiophene) analogues of RITA under mild conditions. These novel analogues showed notable antiproliferative activity against cancer cell lines with wild-type p53 (i.e., HCT116, A549, MCF-7 and K562), but much less activity in HCT116/p53-/- cells. In particular, compound 1f demonstrated promising antiproliferative activity compared to RITA, with IC50 = 28 nM in MCF-7 vs. 54 nM for RITA, and cancer cell selectivity. Compound 1f markedly activated p53 in HCT116 cells at 100 nM, triggering apoptosis. Importantly, we found that both RITA and compound 1f induced G 0/G1 cell cycle arrest by up-regulating miR-34a, which in turn down-regulated the expression of cell cycle-related proteins CDK4 and E2F1. In summary, this study reports an effective synthetic approach for RITA and its analogues, and elucidates a novel antiproliferative mechanism of these compounds. The Royal Society of Chemistry 2012.

Thiophene-substituted fulleropyrrolidine derivatives as acceptor molecules in a thin film organic solar cell

A study of the design of thiophene-substituted fulleropyrrolidine derivatives as the acceptor in photovoltaic cells has been carried out using poly(3-hexylthiophene) (P3HT) as the model donor polymer. It was found that five types of thiophene-substituted fulleropyrrolidine worked as a good acceptor partner with P3HT, and the highest power conversion efficiency (PCE) was obtained for 1-(2-(2-methoxyethoxy)ethyl)-2-(2-thiophen-2-yl)fulleropyrrolidine (2.99%); this is superior to that of the P3HT polymer including methyl [C60]-PCBM under the same experimental conditions.

Dicyanovinyl-substituted oligothiophenes: Structure-property relationships and application in vacuum-processed small molecule organic solar cells

Efficient synthesis of a series of terminally dicyanovinyl (DCV)-substituted oligothiophenes, DCVnT 1-6, without solubilizing side chains synthesized via a novel convergent approach and their application as electron donors in vacuum-processed m-i-p-type planar and p-i-n-type bulk heterojunction organic solar cells is described. Purification of the products via gradient sublimation yields thermally highly stable organic semiconducting materials in single crystalline quality which allows for X-ray structure analysis. Important insights into the packing features and intermolecular interactions of these promising solar cell materials are provided. Optical absorption spectra and electrochemical properties of the oligomers are investigated and valuable structure-property relationships deduced. Photovoltaic devices incorporating DCVnTs 4-6 showed power conversion efficiencies up to 2.8% for planar and 5.2% for bulk heterojunction organic solar cells under full sun illumination (mismatch corrected simulated AM 1.5G sunlight). The 5.2% efficiency shown here represents one of the highest values ever reported for organic vacuum-deposited single heterojunction solar cells.