Novel BODIPY photosensitizers were developed for imaging-guided photodynamic therapy. The introduction of a strong electron donor to the BODIPY core through a phenyl linker combined with the twisted arrangement between the donor and the BODIPY acceptor is essential for reducing the energy gap between the lowest singlet excited state and the lowest triplet state (DE ST ), leading to a significant enhancement in the intersystem crossing (ISC) of the BODIPYs. Remarkably, the BDP-5 with the smallest DE ST (ca. 0.44 eV) exhibited excellent singlet oxygen generation capabilities in both organic and aqueous solutions. BDP-5 also displayed bright emission in the far-red/near-infrared region in the condensed states. More importantly, both in vitro and in vivo studies demonstrated that BDP-5 NPs displayed a high potential for photodynamic cancer therapy and bioimaging.

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The design and development of new pyrene-based fluorescent probes, P-Hcy-1 and P-Hcy-2, which display selective fluorescence enhancements in response to homocysteine (Hcy), are described. The distinctly different fluorescence responses of P-Hcy-1 and P-Hcy-2 to Hcy vs. Cys are explained by theoretical calculations. Finally, the results of cell experiments show that these probes can be used to selectively detect Hcy in mammalian cells.

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A new fluorescein derivative 1 bearing a boronic acid group was investigated as a fluorescent chemosensor for F-. An off-on type fluorescence enhancement was observed by the blocking of the photoinduced electron transfer mechanism, which was induced by the interaction between fluoride and boronic acid moiety.

Three o-phenylendiamine (OPD) derivatives, containing 4-chloro-7-nitrobenzo[c][1,2,5]oxadiazole (NBD-OPD), rhodamine (RB-OPD), and 1,8-naphthalimide (NAP-OPD) moieties, were prepared and tested as phosgene chemosensors. Unlike previously described methods to sense this toxic agent, which rely on chemical processes that transform alcohols and amines to respective phosphate esters and phosphoramides, the new sensors operate through a benzimidazolone-forming reaction between their OPD groups and phosgene. These processes promote either naked eye visible color changes and/or fluorescence intensity enhancements in conjunction with detection limits that range from 0.7 to 2.8 ppb. NBD-OPD and RB-OPD-embedded polymer fibers, prepared using the electrospinning technique, display distinct color and fluorescence changes upon exposure to phosgene even in the solid state.

Hypochlorite (OCl(-)) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl(-) at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl(-) recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl(-) in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl(-), displayed a selective fluorescent off/on response to OCl(-) with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl(-) in live RAW 264.7 cells via two-photon microscopy.