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

Molecules

DamirA. Safin¹  LarisaE. Alkhimova¹  MariaG. Babashkina² 

[1] Institute of Chemistry, University of Tyumen, Volodarskogo Str. 6, 625003 Tyumen, Russia;Institute of Condensed Matter and Nanosciences, Université Catholique de Louvain, Place L. Pasteur 1, 1348 Louvain-la-Neuve, Belgium;

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

DOI  :  10.3390/molecules26113112

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown