Journal ArticleDOI
Resonance Assisted Hydrogen Bonding Phenomenon Unveiled through Both Experiments and Theory: A New Family of Ethyl N-Salicylideneglycinate Dyes
Dinara S. Shapenova,Alexey A. Shiryaev,Michael Bolte,Mercedes Kukułka,Dariusz W. Szczepanik,James Hooper,Maria G. Babashkina,Ghodrat Mahmoudi,Mariusz P. Mitoraj,Damir A. Safin +9 more
TLDR
It is determined, that the electron-withdrawing NO 2 in 4 amplifies the most RAHB effect causing the breaking of the O-H∙�’∙N hydrogen bond and accordingly formation of the dominant cis -keto isomer in both the solid state and EtOH.Abstract:
Extensive experimental and theoretical investigations are reported on the nature of resonance-assisted hydrogen bonding phenomenon (RAHB) and its influence on photophysical properties of the newly designed dyes differing in donor-acceptor properties, namely ethyl N-salicylideneglycinate (1), ethyl N-(5-methoxysalicylidene)glycinate (2), ethyl N-(5-bromosalicylidene)glycinate (3) and ethyl N-(5-nitrosalicylidene)glycinate (4). All compounds are thermochromic in the solid state and they contain a typical intramolecular O-H⋅⋅⋅N hydrogen bond formed between the hydroxyl hydrogen atom and the imine nitrogen atom, yielding the enol form in the solid state. It is unveiled, that the magnitude of RAHB effect fine tunes the strength of the O-H⋅⋅⋅N bonding and accordingly the relative populations of the enol, cis-keto and trans-keto forms leading to variation of the photophysical properties of 1-4. It is determined, that the electron-withdrawing NO2 in 4 amplifies the most RAHB effect causing the breaking of the O-H⋅⋅⋅N hydrogen bond and accordingly formation of the dominant cis-keto isomer in both the solid state and EtOH. To this end, the UV/Vis spectra of 1-3 in EtOH revealed the exclusive presence of the enol form, while the prevalent contribution of the cis-keto form was found for 4. Furthermore, only compound 4 is emissive in the solid state in ambient condition due to dual emission arising from the cis-keto* and trans-keto* forms, while 2 was found to be highly emissive in EtOH. It is revealed qualitatively and quantitatively, based on the ETS-NOCV charge and energy decomposition scheme and the EDDB population-based method, that RAHB is strongly a non-local phenomenon based on electrons pumping or sucking through both the π- and σ-channels, which accordingly exerts chemical bonding changes at both the phenyl ring and predominantly a distant O-H⋅⋅⋅N area.read more
Citations
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Journal ArticleDOI
A chiral (1 R ,2 R )- N , N ′- bis -(salicylidene)-1,2-diphenyl-1,2-ethanediamine Schiff base dye: synthesis, crystal structure, Hirshfeld surface analysis, computational study, photophysical properties and in silico antifungal activity
Alexey A. Shiryaev,Anastasiya N. Goncharenko,Tatyana M. Burkhanova,Larisa E. Alkhimova,Maria G. Babashkina,Ravikumar Chandrasekaran,Damir A. Safin,Damir A. Safin +7 more
TL;DR: In this article, a chiral (1R,2R)-N,N′-bis-(salicylidene)-1,2-diphenyl-1, 2-ethanediamine Schiff base dye (1) was found to be in the enol-imine tautomer, stabilized by two intermolecular O−H···N hydrogen bonds.
Journal ArticleDOI
Naphthalene-based bis-N-salicylidene aniline dyes: Crystal structures, Hirshfeld surface analysis, computational study and molecular docking with the SARS-CoV-2 proteins
Tatyana M. Burkhanova,Maria G. Babashkina,Tugba Taskin-Tok,Artem V. Sharov,Damir A. Safin,Damir A. Safin +5 more
TL;DR: In this paper, structural and computational studies of a series of bis-N-salicylidene aniline dyes, namely N,N′-bis-al-idene-1,5-diaminonaphthalene (1), N, N′-bi-bis(3-hydroxysalicylIDene)-1, 5-Diaminoniaphthalenes (2) and N, n′-is-bis (3-methoxysalICylidenes)-1.5-DIA-
Journal ArticleDOI
Novel sterically demanding Schiff base dyes: An insight from experimental and theoretical calculations
Damir A. Safin,Damir A. Safin,Maria G. Babashkina,Michael Bolte,Aleksandra L. Ptaszek,Mercedes Kukułka,Mariusz P. Mitoraj +6 more
TL;DR: In this paper, structural and photophysical properties of two new bulky base dyes 1 and 2, obtained from the reaction of cyclohexylamine with the 5-bromosalicylaldehyde or 2-hydroxy-1-naphthaldehyde, were investigated.
Journal ArticleDOI
Photophysical properties of ethyl N-(5-bromosalicylidene)glycinate and ethyl N-(5-nitrosalicylidene)glycinate in CH2Cl2
Alexey A. Shiryaev,Tatyana M. Burkhanova,Ghodrat Mahmoudi,Maria G. Babashkina,Damir A. Safin +4 more
TL;DR: In this paper, photophysical studies of two Schiff bases, namely, ethyl N-(5-bromosalicylidene)glycinate (1) and ethyl n-nitrosalicylidsene (2), were performed in the presence of trimethylamine in the ethanol medium.
Journal ArticleDOI
Effects of substitution and conjugation on ESIPT behavior of Schiff base derivatives.
TL;DR: In this paper , the electron-donating of substituents and conjugation effects on the photophysical properties and ESIPT process of the Schiff base derivatives are investigated by theoretical methods.
References
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