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This study aims to describe the design and synthesis of two novel azo and imine chromophores-based dyes derived from two different aldehydes with intramolecular colour matching that are pH sensitive.

The visible absorption wavelength (λ_max) was extended when azo chromophore was included in imine-based systems. The dyed patterns created sophisticated colour-changing paper packaging sensors with pH-sensitive chromophores using alum as a mediator or mordant. Due to the tight adhesive bonding, the dyes on paper’s cellulose fibres could not be removed by ordinary water even at extremely high or low pH, which was confirmed by scanning electron microscopy analysis. The dyed patterns demonstrated an evident, sensitive and fast colour-changing mechanism with varying pH, from pale yellow to red for Dye-I and from pale yellow to brown-violet for Dye-II.

The λ_max for colour changing was recorded from 400 to 490 nm for Dye-I, whereas from 400 to 520 for Dye-II. The freshness judgement of food was checked using actual experiments with cooked crab spoilage, where the cooked crab was incubated at 37 ^oC for 6 h to see the noticeable colour change from yellow to brown-violet with Dye-II. The colour-changing mechanism was studied with Fourier transform infrared (FTIR) spectra at different pH, and thin layer chromatography, nuclear magnetic resonance and FTIR spectroscopy studied the desired structure formation of the dyes. Potential uses for smart packaging sensors include quickly detecting food freshness during transportation or right before consumption.

1. Two novel azo-imine dyes have been synthesized with a pH-responsive effect. 2. The pH-responsive mechanism was studied. 3. The study was supported by computational chemistry using density functional theory. 4. The obtained dyes were used to make pH-responsive sensors for seafood packaging to judge the freshness.

The purpose of this paper is to use the bio-based resource as the starting material for the synthesis of azo dye. Cardanol is one of the most used bio-based resources for carrying out the synthesis of various compounds having numerous end applications. The study presents an attempt to develop an azo dye from Cardanol having end applications in pH-responsive dyes.

The cardanol was sulfonated to block the para position by which ortho positioned hydroxyl group after diazotization and coupling will provide necessary pH-sensitivity. The diazotization of two naphthalene derivatives, i.e. 1-naphthol-8-amino-3,6-disulfonic acid (H-acid) and 7-amino-4-hydroxy-2-naphthalene sulfonic acid (J-acid) was carried out using the standard practice, and the diazotized compounds were coupled with the sulfonated cardanol. The obtained dyes were characterized by Fourier transform infrared, nuclear magnetic resonance, carbon-hydrogen-nitrogen-sulfur analysis and hydroxyl value. The colour properties were checked using UV-vis spectrophotometry and density functional theory, while thermogravimetric analysis was used for the thermal degradation studies of both the dyes.

Water-soluble cardanol-based azo dyes were prepared successfully having good thermal stability, and the obtained results are being presented in this paper.

The originality lies between the use of cardanol as a bio-based resource for the synthesis of azo-dye and the obtained azo-dye has the pH-sensitivity.