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
Product Name
2,2′:5′,2′′-Terthiophene, 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
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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.
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.
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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Synthesis and characterization of an electrochromic copolymer based on 2, 2′ : 5′ , 2″ -terthiophene and 3, 4-ethylenedioxythiophene
Ahmed MS, et al.
Applied Nanoscience, 2(2), 133-141 (2012)
Generation of singlet oxygen by 2,2:5,2-terthiophene and some of its derivatives.
Ciofalo M, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 83(1), 1-6 (1194)
Sanami Yazaki et al.
Journal of the American Chemical Society, 132(22), 7702-7708 (2010-05-15)
New molecular materials combining ionic and electronic functions have been prepared by using liquid crystals consisting of terthiophene-based mesogens and terminal imidazolium groups. These liquid crystals show thermotropic smectic A phases. Nanosegregation of the pi-conjugated mesogens and the ionic imidazolium
Bulletin of the Chemical Society of Japan, 66, 2960-2960 (1993)
M J Perich et al.
Journal of the American Mosquito Control Association, 11(3), 307-310 (1995-09-01)
Application of Tagetes minuta floral extract to silica gel column chromatography produced 2 fractions with the hydrogenate part 20-30 times more toxic to larvae and 12-13 times more toxic to adults of Aedes aegypti and Anopheles stephensi, respectively, than the
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