The widespread concerns about the environmental problems caused by conventional plastic food packaging and food waste led to a growing effort to develop active and intelligent systems produced from renewable biodegradable polymers for food packaging applications. Among intelligent systems, the most widely used are pH indicators, which are generally based on a pH-sensitive dye incorporated into a solid support. The objective of this study was to develop new intelligent systems based on renewable biodegradable polymers and a new bio-inspired pH-sensitive dye. The structure of the dye was elucidated through FT-IR and 1D and 2D NMR spectroscopic analyses. UV-VIS measurements of the dye solutions at various pH values proved their halochromic properties. Their toxicity was evaluated through theoretical calculations, and no toxicity risks were found. The new anthocyanidin was used for the development of biodegradable intelligent systems based on chitosan blends. The obtained polymeric films were characterized through UV-VIS and FT-IR spectroscopy. Their thermal properties were assessed through a thermogravimetric analysis, which showed a better stability of chitosan–PVA–dye and chitosan–starch–dye films compared to those of chitosan–cellulose–dye films and the dye itself. The films’ sensitivity to pH variations was evaluated through immersion in buffer solutions with pH values ranging from 2 to 12, and visible color changes were observed.

The development of biopolymer-based films represents a promising direction in the packaging industry that responds to stringent needs for sustainability, reducing the ecological impact. Traditional fossil-derived polymers present major concerns because of their long decomposition time and their significant contribution to the pollution of the environment. On the contrary, biopolymers such as chitosan, PVA, and PLA offer viable alternatives. This study aimed to obtain an innovative pH indicator for smart packaging using a synthetic non-toxic anthocyanin analogue dye incorporated in bio-based films to indicate meat freshness and quality. The pH-responsive color-changing properties of the dye make it suitable for developing intelligent films to monitor food freshness. The obtained polymeric films were characterized by FT-IR and UV–VIS spectroscopy, and their thermal properties were assessed using thermogravimetric methods. Moisture content, swelling capacity, and water solubility of the polymeric films were also evaluated. The sensitivity of the biopolymer–flavylium composite films to pH variations was studied in the pH range of 2 to 12 and noticeable color variations were observed, allowing the monitoring of the meat’s quality damage through pH changes. The pH-responsive films were applied directly on the surface or in the proximity of pork and chicken meat samples, to evaluate their colorimetric response to fresh and spoilt meat. This study can be the starting point for creating more durable packaging solutions leading to a circular economy.

Given the natural origins of flavylium derivatives, their chemical modifications, and their large potential uses in food, medicine, or green chemistry, the present review is a comprehensive study of flavylium-derived compounds. Several topics such as the green extraction and isolation techniques of flavylium derivatives including their chemical modifications and various characterization tools such as NMR, HPLC, and mass spectrometry are discussed in the review. Furthermore, the use of these derivatives in medicine, food, and materials science is presented, highlighting their relevance and the need for further investigation. Therefore, by examining the advantages and disadvantages of natural and synthetic sources, the review asserts the increased relevance of flavylium-based compounds in active molecules.

PH-responsive indicator films for intelligent food packaging applications are based on the embedding of a natural or synthetic dye in a polymeric substrate, preferably biobased and biodegradable. Although natural colorants like anthocyanins were extensively investigated in this respect, nature-inspired synthetic flavylium compounds could represent an alternative based on their higher stability. In this work, five novel synthetic 4′-aminoflavylium derivatives with different substitution patterns in the benzopyrylium core (compounds 1–5) were synthesized and characterized. Polyvinyl alcohol (PVA), as well as chitosan–PVA and chitosan–starch blends, were used to prepare pH-responsive indicator films having inserted each of the synthesized flavylium dyes or a natural onion peel extract. The PVA films with compounds 1 and 3, and the PVA–chitosan film with compound 1, exhibited antioxidant activity, highlighting their potential for active packaging applications. All indicator films showed pH responsiveness in the range of 2 to 12 and were subsequently tested in contact with the packaging atmosphere or in direct contact with pork and fish meat, at different temperatures (4 °C, 20 °C, and 40 °C) for 24 h to assess their colorimetric response to progressive spoilage. Although the differences were small, the films with the 7-hydroxy-4′-aminoflavylium derivative exhibited the earliest and most intense color change during storage of meat, starting from direct contact at 4 °C for 24 h, being able to identify the initial stages of meat spoilage, while the performance of the dihydroxy-substituted derivative was attenuated by incorporation in polymer matrices. This behavior was comparable to that of onion peel extract, but the synthetic flavylium derivative was more stable. The results can provide new opportunities for intelligent food packaging applications using biopolymer indicator films with 4′-aminoflavylium derivatives.