Structural and Spectroscopic Properties of Benzoylpyridine-Based Hydrazones.
density functional calculations
hydrazones
photochromism
refractive index
vibrational spectra
Journal
Chemphyschem : a European journal of chemical physics and physical chemistry
ISSN: 1439-7641
Titre abrégé: Chemphyschem
Pays: Germany
ID NLM: 100954211
Informations de publication
Date de publication:
17 03 2021
17 03 2021
Historique:
revised:
24
12
2020
received:
14
11
2020
pubmed:
18
2
2021
medline:
18
2
2021
entrez:
17
2
2021
Statut:
ppublish
Résumé
Photochromic hydrazones are attracting the attention in the field of photochromic systems especially due to their P-type character. To understand the structural features and their correlation with the spectroscopic data, UV-Vis, vibrational and ellipsometry spectroscopic techniques are employed with the support of density functional theory (DFT) calculations to three hydrazone derivatives based on benzoylpyridine. Interestingly, analysis of the structure shows the presence of two distinct rotamers around the pyridine ring with different energy and the well-defined conjugation path that changes due to E to Z isomerization especially in the hydrazone -C=N-NH part of the skeleton. IR and Raman spectra are analyzed, showing a higher selectivity in the Z form; moreover, the comparison with the normal modes proves the effect of the reaction on the backbone structure. The experimental results are in good agreement with the theoretical predictions, especially in the case of the Raman spectrum. The molecular polarization also changes from E to Z forms as predicted by DFT calculations. Spectroscopic ellipsometry on thin films of TOPAS doped with 10 %wt of the dimethylamino hydrazone derivative is used to prove such change at the molecular level. A modulation of the refractive index is observed, and it is correlated with the concentration of the active moiety and the calculated electronic polarizabilities.
Identifiants
pubmed: 33595177
doi: 10.1002/cphc.202000941
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
533-541Subventions
Organisme : CUSP
ID : 26240220086
Informations de copyright
© 2021 Wiley-VCH GmbH.
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