Difluoroboron β-diketonate fluorescent dyes for discrimination of volatile organic amines.

Abstract

Volatile organic amines (VOAs) are critical indicators for environmental monitoring and food safety assessment. In this work, we report a difluoroboron β-diketonate-based fluorescent probe (EFHP) with a D-π-A-π-D architecture, exhibiting near-infrared emission and polarity sensitivity. Upon nucleophilic attack by VOAs, the electron-deficient difluoroboron β-diketonate moiety undergoes a specific reaction that disrupts the conjugated structure, resulting in a pronounced fluorescence blue shift. This mechanism was validated by high-resolution mass spectrometry (HRMS) analysis. When loaded onto test paper and polyvinyl alcohol (PVA) hydrogel films, the probe generated four distinct response patterns toward 15 different VOAs. Multivariate statistical analysis demonstrated effective differentiation of VOAs by the probe. The PVA film-based sensor exhibited excellent quantitative performance toward n-propylamine (NPA), with two linear response ranges (0-400 μM and 480-1040 μM), a detection limit of 64 μM, and a rapid response time of 330 s. This work presents a comprehensive strategy integrating molecular probe design with multidimensional data analysis for practical VOAs detection applications.

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