Effect of substituents on cation-receptor properties of crown-containing 1-hydroxyanthraquinone imines

作者: A. A. Kudrevatykh , D. A. Neznaeva , T. P. Martyanov , L. S. Klimenko

DOI: 10.1007/S11172-019-2465-8

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摘要: Complex formation properties of new crown-containing 1-hydroxyanthraquinone imines with donor and acceptor substituents in the anthraquinone nucleus were studied. The compounds prepared by photochemical reactions 4-aminobenzo-15-crown-5-ether photoactive derivatives 1-phenoxyanthraquinone. It has been established that introduction causes a shift prototropic tautomeric imine-enamine equilibrium towards NH-form. As result, significant cation-induced spectral changes are observed during complex formation.

参考文章(17)
Zeliha Hayvali, Mustafa Hayvali, Zeynel Kiliç, Tuncer Hökelek, Edwin Weber, New Benzo-15-Crown-5 Ethers Featuring Salicylic Schiff Base Substitutions – Synthesis, Complexes and Structural Study Journal of Inclusion Phenomena and Macrocyclic Chemistry. ,vol. 45, pp. 285- 294 ,(2003) , 10.1023/A:1024568309739
Alexandr V. Yatsenko, Victor A. Tafeenko, Sergei G. Zhukov, Sergei V. Medvedev, Sergei I. Popov, Structures and tautomeric interconversions of anthraquinone imine derivatives Structural Chemistry. ,vol. 8, pp. 197- 204 ,(1997) , 10.1007/BF02263507
Nina P. Gritsan, Lubov' S. Klimenko, Zoya V. Leonenko, II'ya Ya. Mainagashev, Victor I. Mamatyuk, Valerii P. Vetchinov, Experimental and quantum chemical study of the reactions of 1,10-anthraquinones with alcohols and amines Tetrahedron. ,vol. 51, pp. 3061- 3076 ,(1995) , 10.1016/0040-4020(95)00046-B
Liudmil M. Antonov, Vanya B. Kurteva, Svilen P. Simeonov, Vera V. Deneva, Aurelien Crochet, Katharina M. Fromm, Tautocrowns: a concept for a sensing molecule with an active side-arm Tetrahedron. ,vol. 66, pp. 4292- 4297 ,(2010) , 10.1016/J.TET.2010.04.049
V. Deneva, N. Burdzhiev, E. Stanoeva, L. Antonov, Tautocrowns: Aza-15-Crown Moiety Conjugated to a Tautomeric Schiff Base Spectroscopy Letters. ,vol. 43, pp. 22- 27 ,(2010) , 10.1080/00387010903260273
Evgeny N Ushakov, Artem I Vedernikov, Michael V Alfimov, Sergey P Gromov, None, Regio- and stereospecific [2+2] photocyclodimerization of a crown-containing butadienyl dyevia cation-induced self-assembly in solution Photochemical and Photobiological Sciences. ,vol. 10, pp. 15- 18 ,(2011) , 10.1039/C0PP00227E
A N Uglov, A Bessmertnykh-Lemeune, R Guilard, A D Averin, I P Beletskaya, Optical methods for the detection of heavy metal ions Russian Chemical Reviews. ,vol. 83, pp. 196- 224 ,(2014) , 10.1070/RC2014V083N03ABEH004414
Alexander D. Dubonosov, Vladimir I. Minkin, Vladimir A. Bren, Evgenii N. Shepelenko, Alexey V. Tsukanov, Andrey G. Starikov, Gennadii S. Borodkin, Tautomeric crown-containing chemosensors for alkali-earth metal cations Tetrahedron. ,vol. 64, pp. 3160- 3167 ,(2008) , 10.1016/J.TET.2008.01.096
N.P. Gritsan, L.S. Klimenko, Photochromism of quinoid compounds: Properties of photo-induced ana-quinones Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 70, pp. 103- 117 ,(1993) , 10.1016/1010-6030(93)85030-C
T. P. Martyanov, E. N. Ushakov, V. A. Savelyev, L. S. Klimenko, Crown-containing naphtho- and anthraquinones: synthesis and complexation with alkali and alkaline-earth metal cations Russian Chemical Bulletin. ,vol. 61, pp. 2282- 2294 ,(2012) , 10.1007/S11172-012-0323-Z