Tellurophene

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Tellurophene
Tellurophene.png
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Names
Preferred IUPAC name
Tellurophene [1]
Identifiers
3D model (JSmol)
103225
ChEBI
ChemSpider
647889
PubChem CID
  • InChI=1S/C4H4Te/c1-2-4-5-3-1/h1-4H
    Key: TULWUZJYDBGXMY-UHFFFAOYSA-N
  • C1=C[Te]C=C1
Properties
C4H4Te
Molar mass 179.68 g·mol−1
Appearancepale yellow
Density 2.13
Melting point −36 °C (−33 °F; 237 K)
Boiling point 148 °C (298 °F; 421 K) 714 mm Hg
1.6856
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tellurophene is the organotellurium compound with the formula C4H4Te. It is a heavy analogue of thiophene and selenophene. The compound is a pale yellow liquid. A number of substituted tellurophenes are known. [2]

Contents

Synthesis

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improvedsynthesis

In 1966, Mack report a synthesis of an unsubstituted tellurophene through the reaction of sodium telluride with diacetylene in methanol. This method could be generalised to prepare 2,5-derivatives of tellurophene by selecting a suitably-substituted diacetylene precursor. [3] The product was obtained as a pale yellow liquid with a melting and boiling point of −36 °C and 148 °C, respectively. Taticchi et al. improved upon this synthesis by using a Schlenk line to exclude oxygen and moisture from the reaction vessel, using pure butadiyne (to decrease unwanted oxidation and polymerization side reactions), and by not using a vacuum to remove the methanol as it leads to loss of the product. This improved procedure allowed the tellurophene to be isolated in 47% yield. [4] [5] Hydrogen telluride (HTe-) and tellurols (RTeH) are implicated in these conversions.

Structure and bonding

The geometry of tellurophene was first determined in 1973 through microwave spectroscopy and has been further refined through X-ray diffraction studies. [6] The Te–C bond length is 2.046 Å and the C–Te–C angle is 82°. These findings are consistent with decreased aromaticity vs that of selenophene and related heterocycles. [4] [7]

Reactivity

Tellurophene forms poly(tellurophene) upon treatment with ferric chloride. [8]

C4H4Te + 2 FeCl3 → 1/n[C4H2Te]n + 2 HCl + 2 FeCl2

The conversion, an oxidative polymerization, is modeled after the corresponding synthesis of polythiophene. When treated with halogens, tellurophene gives a Te(IV) derivative:

C4H4Te + Cl2 → C4H4TeCl2

Treatment of tellurophene with tert-butyllithium gives 2-lithiotellurophene. [9]

References

  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 883. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. ↑ Karapala, Vamsi Krishna; Shih, Hong-Pin; Han, Chien-Chung (2018). "Cascade and Effective Syntheses of Functionalized Tellurophenes". Organic Letters . 20 (6): 1550–1554. doi:10.1021/acs.orglett.8b00279. ISSN   1523-7060. PMID   29494165.
  3. ↑ Mack, W. (1966). "Synthesis of Tellurophene and its 2,5-Disubstituted Derivatives". Angew. Chem. Int. Ed. 5 (10): 896. doi:10.1002/anie.196608961.
  4. 1 2 Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo (1977). "Tellurophene and Related Compounds". Advances in Heterocyclic Chemistry Volume 21. Advances in Heterocyclic Chemistry. Vol. 21. pp. 119–173. doi:10.1016/S0065-2725(08)60731-X. ISBN   9780120206216.
  5. ↑ Fringuelli, Francesco; Taticchi, Aldo (1972). "Tellurophen and some of its derivatives". Journal of the Chemical Society, Perkin Transactions 1 : 199–203. doi:10.1039/P19720000199.
  6. ↑ Lukevics, E.; Arsenyan, P.; Belyakov, S.; Pudova, O. (2002). "Molecular Structure of Selenophenes and Tellurophenes". Chemistry of Heterocyclic Compounds . 38 (7): 763–777. doi:10.1023/a:1020607300418. ISSN   0009-3122. S2CID   92305752.
  7. ↑ Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo; Grandolini, Giuliano (1974). "A comparative study of the aromatic character of furan, thiophen, selenophen, and tellurophen". Journal of the Chemical Society, Perkin Transactions 2 . 1974 (4): 332–337. doi:10.1039/P29740000332.
  8. ↑ Sugimoto, Ryu-Ichi; Yoshino, Katsumi; Inoue, Shigehito; Tsukagoshi, Kunimitsu (1985). "Preparation and Property of Polytellurophene and Polyselenophene". Japanese Journal of Applied Physics. 24 (6A): L425. Bibcode:1985JaJAP..24L.425S. doi:10.1143/JJAP.24.L425.
  9. ↑ Jahnke, Ashlee A.; Howe, Graeme W.; Seferos, Dwight S. (2010). "Polytellurophenes with Properties Controlled by Tellurium-Coordination". Angewandte Chemie International Edition. 49 (52): 10140–10144. doi:10.1002/anie.201005664. PMID   21105034.
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