Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
Volume 415, Issue -, Pages -Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2021.113313
Keywords
Pyranoflavylium dyes; Fluorescence; UV-Vis; Acid dissociation constants; pH-sensors; Food packaging
Categories
Funding
- Associate Laboratory for Sustainable Chemistry, Clean Processes, and Technologies LAQV
- FCT [SFRH/BD/136556/2018, UIDB/50006/2020, PTDC/OCE-ETA/31250/2017]
- FEDER [UIDB/50006/2020, PTDC/OCE-ETA/31250/2017]
- Fundação para a Ciência e a Tecnologia [PTDC/OCE-ETA/31250/2017, SFRH/BD/136556/2018] Funding Source: FCT
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Pyranoflavylium-derived compounds have superior properties compared to their flavylium precursors, making them excellent pH indicators. Among them, the symmetrical phenol-based pyranoflavylium dye shows the greatest color variation and remarkable fluorescence properties within the pH range of food spoilage process.
Pyranoflavylium-derived compounds have been shown to have improved properties over the corresponding flavylium precursors, such as chemical and photochemical stability. In addition, they have the characteristic of responding to stimuli like pH due to the proton transfer reactions leading to different colored quinoidal bases. Thus, these dyes can be used as powerful pH-indicators for several sensing applications. In this work, the thermodynamic constants and photophysical properties of novel pyrano-3,7-deoxyanthocyanin dyes bearing phenol and catechol groups were studied by UV-vis absorbance and fluorescence measurements as a function of pH. The cytotoxicity properties of these compounds were also evaluated. Overall, the symmetrical phenol-based pyranoflavylium dye showed the greatest color variation within pH range of food spoilage process, remarkable fluorescence properties, and reduced cytotoxicity, which make it a promising candidate as a pH-dependent colorimetric and fluorescence sensor for food intelligent packaging.
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