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.
Highlights
Schiff base is a condensation product of aldehyde and primary amine
(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
The intermolecular H···H, H···C, and H···O contacts are the dominant contributors to the molecular surface of all the reported compounds. 3 is further described by a remarkable proportion of the intermolecular H···Br contacts
Summary
Schiff base is a condensation product of aldehyde and primary amine. When salicylaldehyde derivative is used as an aldehyde and amine is a monoamine derivative, the condensation yields a NO-Schiff base compound that may produce complexes with a great variety of metal ions upon deprotonation. It is noteworthy that Schiff bases, as well as their corresponding complexes, can possess pronounced bioactivity [4,5,6], including against coronavirus [7]. The latter is becoming even more important since these days humanity is in dire need of drugs for COVID-19 treatment
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