Abstract
Acyl derivatives of 2-aminopyridine, 2-aminopyrimidine, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl, and 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl were obtained from long-chain diacetylenic acyl chlorides and the corresponding heterocyclic compounds. Spreading isotherms of monolayers on a water surface show that lengthening of the hydrocarbon chain and replacement of the pyridyl groups in these compounds by the more hydrophilic pyrimidyl groups render the films more condensed. Long-chain acyl derivatives of nitroxyl radicals form monolayers possesing a low collapse pressure. ESR spectra of Langmuir-Blodgett films of these radicals before and after photopolymerization were recorded.
Similar content being viewed by others
References
V. M. Misin and M. I. Cherkashin,Usp. Khim., 1985,54, 956 [Russ. Chem. Rev., 1985,54 (Engl. Transl.)].
Nonlinear Optical Properties of Organic Molecules and Crystals,2, Eds. D. S. Chemla and J. Zyss, Academic Press, Harcourt Brace Jovanovich Publishers, Orlando, 1987.
I. L. Kotlyarevskii, M. S. Shvartsberg, and L. B. Fisher,Reaktsii atsetilenovykh soedinenii [Reactions of Acetylenic Compounds], Nauka, Novosibirsk, 1967, 315 (in Russian).
Advances in Organic Chemistry,4, Eds. R. A. Raphael, E. C. Taylor, and H. Wynberg, Interscience Publishers, New York-London, 1960.
L. L. Sveshnikova, V. N. Kruchinin, S. F. Vasilevskii, O. M. Usov, and M. S. Shvartsberg,Poverkhnost'[Surface], 1995, in press (in Russian).
M. Suzuki,Thin Solid Films, 1989,180, 253.
E. F. Jenny and J. Druey,Helv. Chim. Acta, 1959,42, 401.
A. M. Sladkov, L. Yu. Ukhin, and V. V. Korshak,Izv. Akad. Nauk SSSR, Ser. Khim., 1963, 2213 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1963, No. 12 (Engl. Transl.)].
E. P. Rozantsev,Svobodnye iminoksil'nye radikaly [Free Iminoxyl Radicals], Khimiya, Moscow, 1976 (in Russian).
J. E. Sohn, A. F. Garito, K. N. Desai, R. S. Narang, and M. Kuryk,Macromol. Chem., 1979,180, 2975.
L. Brandsma,Preparative Acetylenic Chemistry, Elsevier, Amsterdam-Oxford- New York-Tokyo, 1988, 173.
B. Tieke, G. Wegner, D. Naegele, and H. Ringsdorf,Angew. Chem., 1976,88, 805.
V. N. Kruchinin, S. M. Repinskii, L. L. Sveshnikova, E. M. Auvinen, I. N. Domnin, and N. P. Sysoeva,Poverkhnost' [Surface], 1991, 5 (in Russian).
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2009–2012, October, 1995.
The authors are grateful to S. A. Dzyuba for his help in recording ESR spectra and for helpful discussion.
This work was financially supported by the Russian Foundation for Basic Research (Project No. 93-03-04027).
Rights and permissions
About this article
Cite this article
Usov, O.M., Tret'yakov, E.V., Sveshnikova, L.L. et al. Heterocyclic derivatives of long-chain diacetylenic acids. Russ Chem Bull 44, 1929–1932 (1995). https://doi.org/10.1007/BF00707229
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00707229