311073

2,2′:5′,2′′-Terthiophene

99%

• Sinónimos: α-Terthienyl, 2,5-Di(2-thienyl)thiophene
• Fórmula empírica (notación de Hill): C₁₂H₈S₃
• Número de CAS: 1081-34-1
• Peso molecular: 248.39
• Beilstein/REAXYS Number: 178604
• MDL number: MFCD00012167
• UNSPSC Code: 12352103
• PubChem Substance ID: 24858835
• NACRES: NA.23

Propiedades

• assay: 99%
• mp: 93-95 °C (lit.)
• SMILES string: c1csc(c1)-c2ccc(s2)-c3cccs3
• InChI: 1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
• InChI key: KXSFECAJUBPPFE-UHFFFAOYSA-N

Descripción

General description

2,2′:5′,2′′-Terthiophene (3T) is a tri-thiophene based low band conductive polymer that is prepared by reacting 2,5-dibromothiophene and thienylmagnesium bromide in the presence of nickel catalyst.[1][2]

2,2′:5′,2′′-Terthiophene (TTh) may be prepared by nickel catalysed coupling reaction of grignard′s reagent derived from 2-bromothiophene and magnesium.[1] It generates singlet oxygen.[3] In nature, it is found in the floral extract of Tagetes minuta[4] and Echinops grijisii.[5] It is known to be toxic to mosquitoes.[4] It also exihibits antifungal activity.[5]

Application

3T can be combined with 3,4-ethylenedioxythiophene (EDOT) in a tetrabutylammonium perchlorate solution for use as an electrochromic copolymer for a wide range of applications like photovoltaics[6] and polymer light emitting diodes (LEDs).[7][8] It can also be used to form metal-organic based thin films with metals like aluminum, silver, and calcium which can potentially be used for optoelectronics based applications.[9]

Electrochemical copolymerization of carbazole and TTh in sodium perchlorate/acetonitrile was reported.[10] Electrochromic copolymer based on TTh and 3, 4-ethylenedioxythiophene has been reported.[11] TTh acts as a monomer precursor for polythiophene[12] and as a dopant for polycarbonate.[13] It may function as a photosensitizer.[14]

Información de seguridad

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)