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. 2023 Nov 17;13(48):33736-33742.
doi: 10.1039/d3ra05518c. eCollection 2023 Nov 16.

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

Guoxun Zhu  1 , Yan Lin  2 , Wenxian Zhou  3 , Huacan Song  1 , Zhengquan Li  1
Affiliations

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

Guoxun Zhu et al. RSC Adv. .

Abstract

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 (λmax) and larger/smaller half peak width (W1/2). 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 λmax and W1/2 to the chemical shifts obtained by NMR spectroscopy was constructed, which laid the foundation for construction of a spectral library.

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Conflict of interest statement

There are no conflicts of interest to declare.

Figures

Fig. 1
Fig. 1. Some representative azo dyes.
Scheme 1
Scheme 1. Synthetic route of azo compounds.
Fig. 2
Fig. 2. Experimental (a), (c), (e) and theoretical (b), (d), (f) UV-Vis spectra of 3a–c.
Fig. 3
Fig. 3. Visualizations of holes and Ele of 3a–c.
Fig. 4
Fig. 4. Fragment analysis for Hole/Ele of 3a–c.
Scheme 2
Scheme 2. ε, W1/2, and λmax of quantitative spectra.
Fig. 5
Fig. 5. Linear fitting of λmax and W1/2 of 1–5a.
Scheme 3
Scheme 3. Predictive and experimental λmax and W1/2 of 6a–9a.
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