Synthesis and Spectral Properties of Conjugated Bis-1,3-diketo Derivatives of Calix[4]arene in the 1,3-alternate Isomeric Form and Their Complexes with Eu3+

Synthesis and Spectral Properties of Conjugated Bis-1,3-diketo Derivatives of Calix[4]arene in the 1,3-alternate Isomeric Form and Their Complexes with Eu3+ Full article

Journal

Russian Journal of General Chemistry
ISSN: 1070-3632 , E-ISSN: 1608-3350

Output data

Year: 2024, Volume: 94, Number: 7, Pages: 1610-1624 Pages count : 15 DOI: 10.1134/s1070363224070028

Authors

Shvedova А.E. ¹ , Deltsov I.D. ² , Sudakova S.N. ¹ , Masliy A.N. ³ , Syakaev V.V. ¹ , Vatsouro I.M. ⁴ , Mambetova G.Sh. ^1,3 , Kuznetsov A.M. ³ , Kovalev V.V. ⁴ , Mustafina A.R. ¹ , Podyachev S.N. ¹

Affiliations

1	Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia
3	Kazan National Research Technological University, 420015, Kazan, Russia
4	Department of Chemistry, M. V. Lomonosov Moscow State University, 119991, Moscow, Russia

Distally substituted bis-1,3-diketone derivatives of calix[4]arene were synthesized, in which chelate groups are attached via a carbonyl carbon atom to the p-positions of phenolic fragments of a macrocycle fixed in 1,3-alternate isomeric form. 1,3-Diketone derivatives were obtained by acylation of magnesium enolate of a calix[4]arene ketone with 1-benzoylbenzotriazoles. In the synthesized compounds, 1,3-diketone groups are conjugated with the π-aromatic system of calix[4]arene. It was found by means of UV spectroscopy and NMR diffusion methods in combination with quantum chemical (DFT) calculations that a mononuclear complex with bis-chelate coordination of the lanthanide ion is predominantly formed in the solution. The formation of the complex leads to a decrease in the conjugation degree in the ligand. The most effective sensitization of Eu3+ luminescence, compared to the p-F- or p-CF3-phenyl-substituted complexes is observed for calix[4]arene complexes with H-phenyl-substituted 1,3-diketone groups.

Shvedova А.E. , Deltsov I.D. , Sudakova S.N. , Masliy A.N. , Syakaev V.V. , Vatsouro I.M. , Mambetova G.S. , Kuznetsov A.M. , Kovalev V.V. , Mustafina A.R. , Podyachev S.N.
Synthesis and Spectral Properties of Conjugated Bis-1,3-diketo Derivatives of Calix[4]arene in the 1,3-alternate Isomeric Form and Their Complexes with Eu3+
Russian Journal of General Chemistry. 2024. V.94. N7. P.1610-1624. DOI: 10.1134/s1070363224070028 WOS Scopus OpenAlex

Published online:

Aug 30, 2024

Web of science:	WOS:001303636000030
Scopus:	2-s2.0-85202746335
OpenAlex:	W4402080267

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