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. 2020 Sep 29;10(59):35729-35739.
doi: 10.1039/d0ra06934e. eCollection 2020 Sep 28.

Novel edaravone-based azo dyes: efficient synthesis, characterization, antibacterial activity, DFT calculations and comprehensive investigation of the solvent effect on the absorption spectra

Mohammad Amin Davasaz Rabbani  1 , Behzad Khalili  2 , Hamid Saeidian  1
Affiliations

Novel edaravone-based azo dyes: efficient synthesis, characterization, antibacterial activity, DFT calculations and comprehensive investigation of the solvent effect on the absorption spectra

Mohammad Amin Davasaz Rabbani et al. RSC Adv. .

Abstract

The present study deals with designing and synthesizing novel dyes using the drug combination of edaravone and azo compounds which can be used as an indicator for anions and cations. The desired product synthesis was accomplished via a two-step process involving diazotizing the aromatic amines followed by the resultant salts coupling with edaravone. The resulting dyes were obtained with high yields under mild conditions. The structures of the dyes were identified with UV-vis, FT-IR, 1H NMR and 13C NMR spectra and CHN analysis. To investigate the solvatochromism effect, the interaction of different solvents with the selected dyes was evaluated using several parameters including the dielectric constant, refractive index, hydrogen bond donating ability, hydrogen bond accepting ability and dipolarity/polarizability scale. To achieve deep understanding about the stability and geometrical characteristics of the azo-hydrazo tautomers of the synthesized dyes and their UV-visible spectra prediction, some DFT calculations were also carried out on the synthesized dyes. The antibacterial activities of some synthesized compounds were also evaluated using the disk diffusion method. The results revealed different activity of the selected synthesized dyes for antibacterial tests against selected Gram positive and Gram negative bacteria.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. General method for the efficient synthesis of the dyes D1–D10.
Scheme 2
Scheme 2. Proposed mechanism for the formation of novel edaravone-based azo dyes D1–D10.
Fig. 1
Fig. 1. Electronic absorption spectra of dye D2 in different solvents.
Scheme 3
Scheme 3. Azo–hydrazo equilibrium for synthesized dyes.
Scheme 4
Scheme 4. Acid–base equilibrium of the dye D10.
Fig. 2
Fig. 2. Absorption spectra of the dye D10 in acidic and basic solutions.
Fig. 3
Fig. 3. Optimized structures of the dye D2Azo and D2Hydrazo tautomers at B3LYP/6-31+G(d,p) level.
Fig. 4
Fig. 4. Calculated UV-visible spectra for the D2Azo and D2Hydrazo in gas (upper plot) and DMSO (lower plot).
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