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Novel non-aggregated boron-fluorine derivatives with large Stokes shift were facilely synthesized and characterized. These dyes show moderate absorptive coefficients and intense fluorescence emission, and excellent photo-stability in solvents and also in solid state. According to X-ray single-crystal analysis, non-covalent intermolecular interactions provide a rigid structure, which inhibits aggregate formation. These non-aggregated dyes can generate singlet oxygen under light irradiation, which makes them good candidates for photodynamic therapy.

The natural product oleanolic acid (OA) was functionalized and labeled with the non-aggregated fluorescent dye BOPIM (boron 2-(2′-pyridyl)imidazole complex) using ‘click’ chemistry, yielding a highly fluorescent probe. The pharmacological activity of the probe is comparable to that of unmodified OA, making it suitable for studying the therapeutic mechanisms of OA derivatives in vitro.