Study of the electronic effect and quantitative spectra predictions of o -methoxyaniline-terminated monoazonaphthols: a combined experimental and DFT study

A combined experimental and density functional theory (DFT) study on the UV-Vis spectra of o -methoxyaniline-terminated mono azo dyes was conducted. By applying time-dependent-DFT calculations, details of excitation processes were determined and visualization by hole–electron analysis was undertaken...

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Veröffentlicht in:RSC advances 2023-11, Vol.13 (48), p.33736-33742
Hauptverfasser: Zhu, Guoxun, Lin, Yan, Zhou, Wenxian, Song, Huacan, Li, Zhengquan
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Sprache:eng
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Zusammenfassung:A combined experimental and density functional theory (DFT) study on the UV-Vis spectra of o -methoxyaniline-terminated mono azo dyes was conducted. By applying time-dependent-DFT calculations, details of excitation processes were determined and visualization by hole–electron analysis was undertaken. Fragment-divided analysis revealed the contributions of different parts of the structures for the UV-Vis spectra, that richer/poorer electron density on aromatic rings lead to greater/less maximum absorption wavelengths ( λ max ) and larger/smaller half peak width ( W 1/2 ). Combining theoretical prediction with experimental verification, we answered the question of how the electronegativities of substituents affected the electron densities and how it affected the spectra. In addition, a linear model connecting the λ max and W 1/2 to the chemical shifts obtained by NMR spectroscopy was constructed, which laid the foundation for construction of a spectral library.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra05518c