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311073 Sigma-Aldrich

2,2′:5′,2′′-Terthiophene

99%

Synonym: α-Terthienyl, 2,5-Di(2-thienyl)thiophene

  • CAS Number 1081-34-1

  • Empirical Formula (Hill Notation) C12H8S3

  • Molecular Weight 248.39

  •  Beilstein/REAXYS Number 178604

  •  MDL number MFCD00012167

  •  PubChem Substance ID 24858835

  •  NACRES NA.23

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Properties

Related Categories Building Blocks, C10 to C20+, Chemical Synthesis, Heterocyclic Building Blocks, Materials Science,
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.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
WZ9717750
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

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Peer-Reviewed Papers
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References

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