A Family of Ethyl N-Salicylideneglycinate Dyes Stabilized by Intramolecular Hydrogen Bonding: Photophysical Properties and Computational Study

Alkhimova, Larisa E.; Babashkina, Maria G.; Safin, Damir A.

doi:10.3390/molecules26113112

Open AccessArticle

A Family of Ethyl N-Salicylideneglycinate Dyes Stabilized by Intramolecular Hydrogen Bonding: Photophysical Properties and Computational Study

by

Larisa E. Alkhimova

^1,*

,

Maria G. Babashkina

² and

Damir A. Safin

^1,3,4,*

¹

Institute of Chemistry, University of Tyumen, Volodarskogo Str. 6, 625003 Tyumen, Russia

²

Independent Researcher, Respubliki Str. 14, 625003 Tyumen, Russia

³

Kurgan State University, Sovetskaya Str. 63/4, 640020 Kurgan, Russia

⁴

Innovation Center for Chemical and Pharmaceutical Technologies, Ural Federal University Named after the First President of Russia B.N. Eltsin, Mira Str. 19, 620002 Ekaterinburg, Russia

^*

Authors to whom correspondence should be addressed.

Molecules 2021, 26(11), 3112; https://doi.org/10.3390/molecules26113112

Submission received: 23 April 2021 / Revised: 21 May 2021 / Accepted: 21 May 2021 / Published: 23 May 2021

(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2021)

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Abstract

In this work we report solvatochromic and luminescent properties of ethyl N-salicylideneglycinate (1), ethyl N-(5-methoxysalicylidene)glycinate (2), ethyl N-(5-bromosalicylidene)glycinate (3), and ethyl N-(5-nitrosalicylidene)glycinate (4) dyes. 1–4 correspond to a class of N-salicylidene aniline derivatives, whose photophysical properties are dictated by the intramolecular proton transfer between the OH-function and the imine N-atom, affording tautomerization between the enol-imine and keto-enamine forms. Photophysical properties of 1–4 were studied in different pure non-polar and (a)protic polar solvents as well as upon gradual addition of NEt₃, NaOH, and CH₃SO₃H. The DFT calculations were performed to verify the structures of 1–4 as well as their electronic and optical properties.

Keywords: Schiff base; N-salicylidene aniline derivative; photophysical properties; solvatochromism; Hirshfeld surface analysis; DFT

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MDPI and ACS Style

Alkhimova, L.E.; Babashkina, M.G.; Safin, D.A. A Family of Ethyl N-Salicylideneglycinate Dyes Stabilized by Intramolecular Hydrogen Bonding: Photophysical Properties and Computational Study. Molecules 2021, 26, 3112. https://doi.org/10.3390/molecules26113112

AMA Style

Alkhimova LE, Babashkina MG, Safin DA. A Family of Ethyl N-Salicylideneglycinate Dyes Stabilized by Intramolecular Hydrogen Bonding: Photophysical Properties and Computational Study. Molecules. 2021; 26(11):3112. https://doi.org/10.3390/molecules26113112

Chicago/Turabian Style

Alkhimova, Larisa E., Maria G. Babashkina, and Damir A. Safin. 2021. "A Family of Ethyl N-Salicylideneglycinate Dyes Stabilized by Intramolecular Hydrogen Bonding: Photophysical Properties and Computational Study" Molecules 26, no. 11: 3112. https://doi.org/10.3390/molecules26113112

APA Style

Alkhimova, L. E., Babashkina, M. G., & Safin, D. A. (2021). A Family of Ethyl N-Salicylideneglycinate Dyes Stabilized by Intramolecular Hydrogen Bonding: Photophysical Properties and Computational Study. Molecules, 26(11), 3112. https://doi.org/10.3390/molecules26113112

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A Family of Ethyl N-Salicylideneglycinate Dyes Stabilized by Intramolecular Hydrogen Bonding: Photophysical Properties and Computational Study

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