A water caged BODIPY as fluorescence sensor of phthalates

Abstract Phthalates esters (PAEs) have been used as plasticizers, which contributes to some cancers and endocrine dyscrasia. Here we reported a BODIPY fluorescent dye ((3-(4-(5,5-difluoro-2-(4-(hydroxymethyl)phenyl))-1,3,7,9-tetramethyl-5H-5l4,6l4-Bispyrrole[1,2-c:2′,1′-f] [1,3,2]borothiaserine-10-yl)phenyl)-2-(4-nitro)phenylnier (BCNOH)) modified with p-nitrodiphenylacrylonitrile, and hydroxymethyl phenyl group for the affinity and sensing of PAEs. BCNOH formed non-emission water caged BCNOH, which was turned on by PAEs. Fluorescence, UV and Density functional theory (DFT) calculation were performed to research the mechanism. Results demonstrate that PAEs assembled with water caged BCNOH producing nano fluorescence dyes (nano-BCNOH), in which BCNOH is E isomerization. The binding ratio of BCNOH and DBP is 1:10, and the detection limit of PAEs is related to the chain length of phthalates. Hydroxymethyl phenyl group of BCNOH increased the attachment with DBP, and the interaction of DBP and p-nitrodiphenylacrylonitrile was the trigger to turn on the fluorescence emission. Moreover, the water caged BCNOH was used for the detection of PAEs in rice yellow wine and liquor and spirits. Results indicate that attenuating the isomerization of water caged BODIPY dyes will be a potential strategy for the development of turn-on fluorescence sensors.