Perylene dyes have found widespread applications as organic materials because of their unique optical properties, excellent thermo- and photo-stability, and low toxicity. However, the application of perylene dyes as fluorescent probes remains largely unexplored due to their tendency to form non-fluorescent aggregates in aqueous solution. We have reported an supramolecular approach to prevent aggregation of perylene monomide in aqueous solution by forming host-guest complexes with cucurbit[8]uril (CB[8]). Here, we report the design and synthesis of water-soluble perylene monoimides (PMI1 and PMI2) with red to near-infrared (red-NIR) emission and large stokes shift. The fluorescence emission of PMI1 and PMI2 is very low in aqueous solvent due to the aggregation effect. Upon encapsulation with CB[8], the fluorescence intensity of these dyes increased about 10-fold with preserved red-NIR emission and large stokes shift. We further demonstrated the capability of these supramolecular fluorescent complexes to serve as fluorescent probes for detection of addictive drugs in urine sample.

Cucurbit[8]uril and perylene-based red-NIR host-guest complexes for detection of drugs in urine sample

2019 Spring National Meeting

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