Terthiophene

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.

Terthiophene
Terthiophene
Names
Preferred IUPAC name
12,22:25,32-Terthiophene
Other names
α-Terthienyl
2,5-Di(2-thienyl)thiophene
Identifiers
3D model (JSmol)
178604
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.168.218
EC Number
  • 640-441-1
KEGG
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 checkY
    Key: KXSFECAJUBPPFE-UHFFFAOYSA-N checkY
  • 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
Appearance pale yellow solid
Melting point 93-95 °C
insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 flammable
GHS labelling:[1]
GHS07: Exclamation mark
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).
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Infobox references

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

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.
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