Development of imine-azo-dyes derived from vanillin and salicylaldehyde for pH-sensing in smart packaging

Abstract

Purpose 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. Design/methodology/approach 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. Findings 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 o C 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. Originality/value 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.