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BODIPY fluorophores are popular functional dyes in a multitude of fields in chemistry, physics, and materials sciences due to their excellent properties such as a good photostability, high fluorescence quantum yields, and almost unlimited possibilities for tailoring their properties by chemical functionalization. In sensing applications, BODIPY dyes are widely employed.
In this work, we present an approach for creating a BODIPY-based pocket-like structure for the recognition of volatile organic compounds (VOC) such as benzene and its derivatives. This may lead to the development of sensing devices for this class of compounds, which receive special attention by environmental chemists and regulatory authorities due to severe adverse effects on humans in particular and the environment in general. The low reactivity of benzene-derived hazardous compounds is thereby a major fact that has to be taken into consideration. While for other reactive gaseous compounds, fluorophore-based detection performance is achieved by the chemical modification of the fluorophore itself, e.g. by bond cleavage, addition, oxidation or reduction reactions; this is not possible for many VOCs. Several metal complexes were described for the sensing of benzene and its derivatives, but no organic dyes such as BODIPYs are known with these capabilities. Our unique concept towards BODIPY-based molecules acting as scavengers for VOCs is supposed to overcome the problem of benzene’s low reactivity by enforcing π-π-interactions between the fluorophore and the volatile aromatic analyte in pocket-like molecular structures.
Fluorescence based sensing is a versatile approach for the trace analysis outside of the laboratory, requiring suitable sensor materials and their integration into sensing devices. The versatility of fluorophores as probes, especially in terms of the possibility to tailor their optical as well as their recognition properties by synthetic modifications in a wide range, renders them a superior active component for the preparation of optical sensor devices. Recent works at BAM in this field include, for example, the detection of nerve gas agents, illustrating impressively the aforementioned benefits of fluorophores in optical sensing applications.
In the interdisciplinary approach presented here, we target hazardous gases such as ammonia, benzene, and hydrogen sulfide, next to others, which pose a major threat to human health and environmental safety and for which the availability of a sensitive and reliable detection method is highly desirable.
The dyes presented follow a “turn-on” fluorescence schematic which allows for the selective and sensitive detection of the respective gaseous analyte. The immobilization of the probe in polymeric matrices is then the next step toward the fabrication of a prototype device for molecular sensing.