Resonance Assisted Hydrogen Bonding Phenomenon Unveiled through Both Experiments and Theory: A New Family of Ethyl N-Salicylideneglycinate Dyes.
DFT modeling
N-salicylidene aniline derivatives
optical properties
resonance assisted hydrogen bonding
π-electrons delocalizations
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
09 Oct 2020
09 Oct 2020
Historique:
received:
31
03
2020
revised:
07
05
2020
pubmed:
20
5
2020
medline:
20
5
2020
entrez:
20
5
2020
Statut:
ppublish
Résumé
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 NO
Identifiants
pubmed: 32428288
doi: 10.1002/chem.202001551
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
12987-12995Subventions
Organisme : Marie Skłodowska-Curie
ID : 797335
Organisme : Polish National Science Center
ID : 2017/26/E/ST4/00104
Organisme : 797335
ID : Marie Skłodowska-Curie Grant Agreement No. 797335 "MulArEffect"
Organisme : Polish National Science Center
ID : Sonata Bis Project 2017/26/E/ST4/00104
Informations de copyright
© 2020 Wiley-VCH GmbH.
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