Terthiophene
{{chembox
| Verifiedfields = changed
| verifiedrevid = 470603009
| Name = Terthiophene
| ImageFile = Alpha-Terthiophene numbering.svg
| ImageName = Terthiophene
| PIN = 12,22:25,32-Terthiophene
| OtherNames = α-Terthienyl
2,5-Di(2-thienyl)thiophene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 1081-34-1
| Beilstein = 178604
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10335
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 90017
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 58578
| EINECS = 640-441-1
| KEGG = C08460
| PubChem = 65067
| RTECS = WZ9717750
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0P77RAU2RR
| InChI = 1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
| InChIKey = KXSFECAJUBPPFE-UHFFFAOYAI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KXSFECAJUBPPFE-UHFFFAOYSA-N
| SMILES = s1cccc1c2sc(cc2)c3sccc3
}}
|Section2={{Chembox Properties
| Formula = C12H8S3
| MolarMass = 248.39 g/mol
| Appearance = pale yellow solid
| Density =
| Solubility = insoluble
| MeltingPt = 93-95 °C
}}
|Section3={{Chembox Structure
| CrystalStruct =
| Dipole =
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards = flammable
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|332+313|337+313|362|403+233|405|501}}
}}
|Section8={{Chembox Related
| OtherCompounds = Thiophene
polythiophene
}}
}}
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.
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.{{ cite journal |author1=Smeets, B. J. J.|author2=Meijer, R. H.|author3=Meuldijk, J.|author4=Vekemans, J. A. J. M.|author5=Hulshof, L. A. |name-list-style=amp | title = Process Design and Scale-Up of the Synthesis of 2,2':5',2"-Terthienyl | journal = Organic Process Research & Development | year = 2003 | volume = 7 | issue = 1 | pages = 10–16 | doi = 10.1021/op020044n }}
Properties and applications
This substance is likely responsible for the insecticidal activity of Tagetes minuta as it can react with light and oxygen to make singlet oxygen.{{ cite journal |author1=Ciofalo, M. |author2=Ponterini, G. | title = Generation of singlet oxygen by 2,2':5',2"-terthiophene and some of its derivatives | journal = Journal of Photochemistry and Photobiology A | year = 1994 | volume = 83 | issue = 1 | pages = 1–6 | id = CODEN: JPPCEJ | issn = 1010-6030 | doi = 10.1016/1010-6030(94)03802-3 }} {{Cite journal
| last1 = Perich | first1 = M. J.
| last2 = Wells | first2 = C.
| last3 = Bertsch | first3 = W.
| last4 = Tredway | first4 = K. E.
| title = Isolation of the insecticidal components of Tagetes minuta (Compositae) against mosquito larvae and adults
| journal = Journal of the American Mosquito Control Association
| volume = 11
| issue = 3
| pages = 307–310
| year = 1995
| pmid = 8551298
}}
Together with derivatives of 2,2'-bithiophene, various chlorinated terthiophenes occur naturally in thistles.{{ cite journal |author1=Liu, Y. |author2=Ye, M. |author3=Guo, H. Z. |author4=Zhao, Y. Y. |author5=Guo, D. A. | title = New thiophenes from Echinops grijisii | journal = Journal of Asian Natural Products Research | year = 2002 | volume = 4 | issue = 3 | pages = 175–178 | id = CODEN: JANRFI | issn = 1028-6020 | pmid = 12118504 | doi = 10.1080/1028602021000000071 |s2cid=41384356 }}
Terthiophene has been employed as building block for the organic semi-conductor polythiophene.
See also
References
{{reflist}}