Excited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions

Spectral-luminescence properties of a hybrid compound containing a coumarin-type spiropyran and an azomethinocoumarin fragment in toluene-acetonitrile solution in the presence of Li<sup>+</sup>, Ca<sup>2+</sup>, Zn<sup>2+</sup> and Mg<sup>2+</sup> ions...

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Autores principales: Natalia L. Zaichenko, Tatyana M. Valova, Olga V. Venidiktova, Alexander V. Lyubimov, Andrey I. Shienok, Liubov S. Koltsova, Anton O. Ayt, Galina V. Lyubimova, Leonid D. Popov, Valery A. Barachevsky
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Publicado: MDPI AG 2021
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Acceso en línea:https://doaj.org/article/de780421141a43718b0d2c978f218011
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spelling oai:doaj.org-article:de780421141a43718b0d2c978f2180112021-11-25T18:28:11ZExcited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions10.3390/molecules262268941420-3049https://doaj.org/article/de780421141a43718b0d2c978f2180112021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6894https://doaj.org/toc/1420-3049Spectral-luminescence properties of a hybrid compound containing a coumarin-type spiropyran and an azomethinocoumarin fragment in toluene-acetonitrile solution in the presence of Li<sup>+</sup>, Ca<sup>2+</sup>, Zn<sup>2+</sup> and Mg<sup>2+</sup> ions are reported. Two excited state proton transfers can occur in the hybrid compound—the transfer of a proton from the OH group of the 7-hydroxy coumarin tautomer to the N atom of the C=N bond of the azomethine fragment leading to green ESIPT fluorescence with a maximum at 540 nm and from the OH group of the 7-hydroxy coumarin tautomer to the carbonyl group of the pyrone chromophore, which leads to the formation of the 2-hydroxyl-tautomer <b>T</b> of coumarin with blue fluorescence with a maximum at 475 nm. Dependence of these excited state proton transfers on the metal nature and irradiation with an external UV source is discussed.Natalia L. ZaichenkoTatyana M. ValovaOlga V. VenidiktovaAlexander V. LyubimovAndrey I. ShienokLiubov S. KoltsovaAnton O. AytGalina V. LyubimovaLeonid D. PopovValery A. BarachevskyMDPI AGarticlefluorescencephotochromismspiropyranazomethinocoumarinexcited state proton transferOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6894, p 6894 (2021)
institution DOAJ
collection DOAJ
language EN
topic fluorescence
photochromism
spiropyran
azomethinocoumarin
excited state proton transfer
Organic chemistry
QD241-441
spellingShingle fluorescence
photochromism
spiropyran
azomethinocoumarin
excited state proton transfer
Organic chemistry
QD241-441
Natalia L. Zaichenko
Tatyana M. Valova
Olga V. Venidiktova
Alexander V. Lyubimov
Andrey I. Shienok
Liubov S. Koltsova
Anton O. Ayt
Galina V. Lyubimova
Leonid D. Popov
Valery A. Barachevsky
Excited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions
description Spectral-luminescence properties of a hybrid compound containing a coumarin-type spiropyran and an azomethinocoumarin fragment in toluene-acetonitrile solution in the presence of Li<sup>+</sup>, Ca<sup>2+</sup>, Zn<sup>2+</sup> and Mg<sup>2+</sup> ions are reported. Two excited state proton transfers can occur in the hybrid compound—the transfer of a proton from the OH group of the 7-hydroxy coumarin tautomer to the N atom of the C=N bond of the azomethine fragment leading to green ESIPT fluorescence with a maximum at 540 nm and from the OH group of the 7-hydroxy coumarin tautomer to the carbonyl group of the pyrone chromophore, which leads to the formation of the 2-hydroxyl-tautomer <b>T</b> of coumarin with blue fluorescence with a maximum at 475 nm. Dependence of these excited state proton transfers on the metal nature and irradiation with an external UV source is discussed.
format article
author Natalia L. Zaichenko
Tatyana M. Valova
Olga V. Venidiktova
Alexander V. Lyubimov
Andrey I. Shienok
Liubov S. Koltsova
Anton O. Ayt
Galina V. Lyubimova
Leonid D. Popov
Valery A. Barachevsky
author_facet Natalia L. Zaichenko
Tatyana M. Valova
Olga V. Venidiktova
Alexander V. Lyubimov
Andrey I. Shienok
Liubov S. Koltsova
Anton O. Ayt
Galina V. Lyubimova
Leonid D. Popov
Valery A. Barachevsky
author_sort Natalia L. Zaichenko
title Excited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions
title_short Excited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions
title_full Excited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions
title_fullStr Excited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions
title_full_unstemmed Excited State Proton Transfers in Hybrid Compound Based on Indoline Spiropyran of the Coumarin Type and Azomethinocoumarin in the Presence of Metal Ions
title_sort excited state proton transfers in hybrid compound based on indoline spiropyran of the coumarin type and azomethinocoumarin in the presence of metal ions
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/de780421141a43718b0d2c978f218011
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