311073

2,2′:5′,2′′-Terthiophene

99%

• Synonym(s): α-Terthienyl, 2,5-Di(2-thienyl)thiophene
• Empirical Formula (Hill Notation): C₁₂H₈S₃
• CAS Number: 1081-34-1
• Molecular Weight: 248.39
• Beilstein/REAXYS Number: 178604
• MDL number: MFCD00012167
• UNSPSC Code: 12352103
• PubChem Substance ID: 24858835
• NACRES: NA.23

Properties

• 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

Description

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.

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

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 and polymer light emitting diodes (LEDs). 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.

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

Safety Information

• 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)