Terthiophene

Last updated
Terthiophene
Alpha-Terthiophene numbering.svg
Names
Preferred IUPAC name
12,22:25,32-Terthiophene
Other names
α-Terthienyl
2,5-Di(2-thienyl)thiophene
Identifiers
  • 1081-34-1 X mark.svgN
3D model (JSmol)
178604
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.168.218 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 640-441-1
KEGG
PubChem CID
RTECS number
  • WZ9717750
UNII
  • InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H Yes check.svgY
    Key: KXSFECAJUBPPFE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
    Key: KXSFECAJUBPPFE-UHFFFAOYAI
  • s1cccc1c2sc(cc2)c3sccc3
Properties
C12H8S3
Molar mass 248.39 g/mol
Appearancepale yellow solid
Melting point 93-95 °C
insoluble
Hazards [1]
Main hazards flammable
GHS pictograms GHS-pictogram-exclam.svg
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds
Thiophene
polythiophene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Terthiophene is the organic compound with the formula [C4H3S]2C4H2S. It is an oligomer of the heterocycle thiophene, a shorter oligomer is dithienyl, and the parent polymer is polythiophene. In the most common isomer of terthiophene, two thienyl groups are connected via their 2 positions to a central thiophene, also at the carbon atoms flanking the sulfur.

Contents

Preparation of terthiophene

Terthiophene is prepared by the nickel- or palladium-catalysed coupling reaction of 2,5-dibromothiophene with the Grignard reagent derived from 2-bromothiophene. [2]

Properties and applications

This isomer is a pigment in African marigolds ( Tagetes spp.) and exhibits some biological activity because it sensitizes the formation of singlet oxygen. [3] It is responsible for the insecticidal activity of Tagetes minuta. [4]

Together with derivatives of 2,2'-bithiophene, various substituted terthiophenes occur naturally. Examples include 5,5''-dichloro-α-terthiophene, 5-chloro-α-terthiophene, 5-acetyl α-terthiophene, and 5-carboxyl bithiophene. [5]

Terthiophene has been employed as building block for the organic semi-conductor polythiophene.

See also

Related Research Articles

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Porphyrin Heterocyclic organic compound with four modified pyrrole subunits

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H
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O
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Benzoxazole Chemical compound

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Thienothiophene

Thienothiophene usually refers to any of three structurally related derivatives of thiophene with the formula C6H4S2. In order of importance, they are: thieno(3,2-b)thiophene, thieno(2,3-b)thiophene, and thieno(3,4-b)thiophene. Other isomers feature S(IV) and are less stable. Thieno[2,3-b]thiophene was the first member of the series to be isolated. It was obtained in very low yield upon heating citric acid, a source of a six-carbon linear chain, with P4S10. More efficient syntheses of this and the other two stable thienothiophenes involve cyclization reactions of substituted thiophenes.

1,2-Dioxolane Chemical compound

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2
)3–O–O–].

References

  1. "2,2':5',2-Terthiophene". pubchem.ncbi.nlm.nih.gov.
  2. Smeets, B. J. J.; Meijer, R. H.; Meuldijk, J.; Vekemans, J. A. J. M. & Hulshof, L. A. (2003). "Process Design and Scale-Up of the Synthesis of 2,2':5',2"-Terthienyl". Organic Process Research & Development. 7 (1): 10–16. doi:10.1021/op020044n.
  3. Ciofalo, M.; Ponterini, G. (1994). "Generation of singlet oxygen by 2,2':5',2"-terthiophene and some of its derivatives". Journal of Photochemistry and Photobiology A. 83 (1): 1–6. doi:10.1016/1010-6030(94)03802-3. ISSN   1010-6030. CODEN: JPPCEJ.
  4. Perich, M. J.; Wells, C.; Bertsch, W.; Tredway, K. E. (1995). "Isolation of the insecticidal components of Tagetes minuta (Compositae) against mosquito larvae and adults". Journal of the American Mosquito Control Association. 11 (3): 307–310. PMID   8551298.
  5. Liu, Y.; Ye, M.; Guo, H. Z.; Zhao, Y. Y.; Guo, D. A. (2002). "New thiophenes from Echinops grijisii". Journal of Asian Natural Products Research. 4 (3): 175–178. doi:10.1080/1028602021000000071. ISSN   1028-6020. PMID   12118504. S2CID   41384356. CODEN: JANRFI.