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Sterically hindered mono- and bis(2,5-diaryloxazoles) containing biphenyl systems

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The condensation of hydrochloric salts of ω-aminomethyl aryl ketones with diphenic anhydride or with the diacid chloride of diphenic acid and subsequent cyclodehydration of the condensation products formed give sterically hindered mono- and bis(2, 5-diaryloxazoles) containing the biphenyl system. The spectroluminescent properties of these compounds were studied. Comparison of the absorption spectra of 2,2′-di(5-phenyloxazolyl-2)biphenyl and 2,5-diphenyloxazole indicates the complete lack of conjugation between the diphenyloxazole fragments, their independent behavior, and their retention of the spatial configuration of 2,5-diphenyloxazole. 2,2′-Di(5-phenyloxazolyl-2)biphenyl has a large Stokes shift. Steric hindrance is also found in 2-carboxy-2′-(5-phenyloxazolyl-2)biphenyl molecules.

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Literature cited

  1. Luminescent Materials and Chemicals. NIITÉKhim Catalog [in Russian], Cherkassy (1975), p. 180.

  2. G. A. Abakumov, V. V. Fadeev, R. V. Khokhlov, and A. P. Simonov, Spectrosc. Lett., 8, 651 (1975).

    Google Scholar 

  3. B. Williamson and W. Rodebush, J. Am. Chem. Soc., 63, 3018 (1941).

    Google Scholar 

  4. O. Bastiansen, Acta Chem. Scand., 3, 408 (1949); 4, 926 (1950).

    Google Scholar 

  5. L. M. Litvinenko and A. P. Grekov, Ukr. Khim. Zh., 20, 194 (1954).

    Google Scholar 

  6. A. G. London and R. Z. Mazengo, Org. Mass Spectrom., 8, 179 (1974).

    Google Scholar 

  7. E. D. Schmid and R. D. Tomsom, J. Am. Chem. Soc., 103, 1628 (1981).

    Google Scholar 

  8. G. H. Beaven and D. M. Hall, J. Chem. Soc., 4637 (1956).

  9. B. M. Krasovitskii and D. G. Pereyaslova, Dokl. Akad. Nauk SSSR, 98, 71 (1957).

    Google Scholar 

  10. R. J. Morris and W. R. Brode, J. Am. Chem. Soc., 70, 2485 (1948).

    Google Scholar 

  11. W. R. Brode and R. J. Morris, J. Org. Chem., 13, 200 (1948).

    Google Scholar 

  12. B. M. Krasovitskii, V. B. Smelyakova, and R. N. Nurmukhametov, Opt. Spektrosk., 17, 558 (1964).

    Google Scholar 

  13. A. C. Littlejohn and J. W. Smith, J. Chem. Soc., 2552 (1954).

  14. R. Roberts and T. Johnson, J. Am. Chem. Soc., 47, 1396 (1925).

    Google Scholar 

  15. C. Graebe and C. Aube, Ann., 247, 257 (1888).

    Google Scholar 

  16. F. Bell and P. H. Robinson, J. Chem. Soc., 1695 (1927).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 184–188, February, 1985.

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Krasovitskii, B.M., Shapiro, S.G. & Yushko, É.G. Sterically hindered mono- and bis(2,5-diaryloxazoles) containing biphenyl systems. Chem Heterocycl Compd 21, 149–153 (1985). https://doi.org/10.1007/BF00504197

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  • DOI: https://doi.org/10.1007/BF00504197

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