Arylidene-imidazolones and their acyclic analogue as fluorescent sensors of metal ions

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Abstract

We report about a series of methylene-imidazolones with complexing groups. The fluorescent properties of these compounds were studied in various solvents as well as in the presence of different salts. We discovered that two of the synthesized substances – hydroxyquinolinidene-imidazolone and difluorobenzimidazolidene-imidazolone – can be used as selective fluorescent sensors for cadmium and zinc ions and potentially as markers for monitoring intracellular processes.

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About the authors

S. A. Krasnova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; National Research University Higher School of Economics

Author for correspondence.
Email: svetlanakr2002@mail.ru
Russian Federation, 117997, Moscow, ul. Miklukho-Maklaya, 16/10; 101000, Moscow, ul. Myasnitskaya, 20

E. R. Zaitseva

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: svetlanakr2002@mail.ru
Russian Federation, 117997, Moscow, ul. Miklukho-Maklaya, 16/10

D. I. Rudik

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Peoples’ Friendship University of Russia named after Patrice Lumumba

Email: svetlanakr2002@mail.ru
Russian Federation, 117997, Moscow, ul. Miklukho-Maklaya, 16/10; 117198, Moscow, ul. Miklukho-Maklaya, 6

D. S. Ivanov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; M. Lomonosov Moscow State University

Email: svetlanakr2002@mail.ru
Russian Federation, 117997, Moscow, ul. Miklukho-Maklaya, 16/10; 119991, Moscow, ul. Leninskiye Gory, 1

A. A. Mikhaylov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: svetlanakr2002@mail.ru
Russian Federation, 117997, Moscow, ul. Miklukho-Maklaya, 16/10

M. S. Baranov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: svetlanakr2002@mail.ru
Russian Federation, 117997, Moscow, ul. Miklukho-Maklaya, 16/10; 117997, Moscow, ul. Ostrovitianova, 1

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Supplementary files

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2. Scheme 1. Scheme of synthesis of arylidene-imidazolones (I–VI) and their acyclic analog (VII) with complexing functional groups.

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3. Fig. 1. Absorption and emission spectra of compounds (III) and (IV) in a mixture of MeCN–H2O in free form and with the addition of Cd2+ and Zn2+ ions.

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4. Additional materials
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