311073
2,2′:5′,2′′-Terthiophene
99%
Synonym(s):
α-Terthienyl, 2,5-Di(2-thienyl)thiophene
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About This Item
Empirical Formula (Hill Notation):
C12H8S3
CAS Number:
Molecular Weight:
248.39
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
178604
Assay:
99%
InChI
1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
SMILES string
c1csc(c1)-c2ccc(s2)-c3cccs3
InChI key
KXSFECAJUBPPFE-UHFFFAOYSA-N
assay
99%
mp
93-95 °C (lit.)
Quality Level
Related Categories
General description
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Kosuke Sawabe et al.
Advanced materials (Deerfield Beach, Fla.), 24(46), 6141-6146 (2012-09-11)
Extremely high current densities are realized in single-crystal ambipolar light-emitting transistors using an electron-injection buffer layer and a current-confinement structure via laser etching. Moreover, a linear increase in the luminance was observed at current densities of up to 1 kA
Synthetic Metals, 62, 233-233 (1994)
Process Design and Scale-Up of the Synthesis of 2,2`:5`,2``-Terthienyl
Smeets BJJ, et al.
Organic Process Research & Development, 7(1), 10-16 (2003)
Electrochemical copolymerization of carbazole and 2,2?:5?-2? terthiophene: characterization and micro-capacitor application
Ates M and Eren N
Iranian Polymer Journal, 23(8), 581-589 null
D Mares et al.
Mycoses, 37(9-10), 377-383 (1994-09-01)
The dermatophyte Microsporum cookei Ajello was treated with nine new natural and synthetic 2,2':5',2"-terthiophenes to determine their possible antifungal activity. In the dark the thiophenes were inactive, while when photoactivated with UV-A they induced a remarkable reduction in the growth
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