Food smart packaging
has emerged as a promising technology to address
consumer concerns regarding food conservation and food safety. In
this context, we report the rational design of azide-containing pyranoflavylium-based
pH-sensitive dye for subsequent click chemistry conjugation toward
a chitosan-modified alkyne. The chitosan-pyranoflavylium conjugate
was characterized by infrared (ATR-FTIR), ultraviolet–visible
(UV–vis), nuclear magnetic resonance (NMR) spectroscopies,
and dynamic light scattering (DLS), as well as its thermodynamic parameters
related to their pH-dependent chromatic features. The fabrication
of thin-films through electrostatic-driven layer-by-layer (LbL) assembly
technology was first screened by quartz crystal microbalance with
dissipation monitoring (QCM-D) onto gold substrates, and then free-standing
(FS) multilayered membranes from polypropylene substrate were obtained
using a homemade automatic dipping robot. The membranes’ characterization
included morphology analysis and thickness evaluation, assessed by
scanning electron microscopy (SEM), pH-responsive color change performance
tests using buffer solutions at different pH levels, and biogenic
amines-enriched model solutions, demonstrating the feasibility and
effectiveness of the chitosan-pyranoflavylium/alginate biomembranes
for food spoilage monitoring. This work provides insights toward the
development of innovative pH-responsive smart biomaterials for advanced
and sustainable technological packaging solutions, which could significantly
contribute to ensuring food safety and quality, while reducing food
waste.