Bioactive flavonoids, the major ingredients of red wines, have been proven to prevent atherosclerosis and cardiovascular disease due to their anti-inflammatory and anti-oxidant activity. However, flavonoids have proven challenging to identify, even when multiple approaches are combined. Hereby, a simple array was constructed to detect flavonoids by employing phenylboronic acid modified perylene diimide derivatives (PDIs). Through multiple non-specific interactions (hydrophilic, hydrophobic, charged, aromatic, hydrogen-bonded and reversible covalent interactions) with flavonoids, the fluorescence of PDIs can be modulated, and variations in intensity can be used to create fingerprints of flavonoids. This array successfully discriminated 14 flavonoids of diverse structures and concentrations with 100% accuracy, based on patterns in fluorescence intensity modulation, via optimized machine learning algorithms. As a result, this array demonstrated the parallel detection of 8 different types and origins of red wines with a high accuracy, revealing the excellent potential of the sensor array in food mixtures detection.
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