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Thiophenols are widely utilized for producing pesticides, polymers and pharmaceuticals. Studies have shown that prolonged exposure of human to thiolphenol can result in serious health problems such as significant damage of the central nervous system. Herein, we have developed a novel turn-on two-photon fluorescent probe TP-ASH for selective and sensitive detection of thiophenols. We first constructed a new two-photon dye by connecting a coumarin fluorophore and a naphthalene fluorophore through 2,5- disubstituted-1,3,4-oxadiazole ring to afford d -π-A-π- d -structure. Fluorescent studies showed that this new dye possess large two-photon active absorption across-section (250 GM) and high fluorescence quantum yield (0.85). Encouraged by the results, we proceeded to conjugate this novel dye to a thiophenol recognition moiety, 4-dinitrobenzene-ether (DNB). The resulting probe displayed high selectivity towards thiophenols over their similar analogues, aliphatic thiols. The probe also exhibited high sensitivity, with a detection limit of 6.7 nM and a fluorescence enhancement of 163-fold. In addition, we have successfully applied the probe for two-photon imaging studies of thiphenols in living cells and mice tissues. We envision that the probe will add useful tools in detecting thiophenols in environmental samples and biological systems. [ABSTRACT FROM AUTHOR]

We report a novel turn-on two-photon fluorescent probe ( TPNF ) for detecting formaldehyde based on aza-Cope rearrangement and intramolecular charge transfer (ICT). The probe, containing a 1,8-naphthalimide dye with a homoallylamino group, has was shown with high selectivity, sensitivity and low cytotoxicity and it was capable of detecting formaldehyde in live cells. Moreover, a time-dependent density functional theory (TD-DFT) calculation was performed to demonstrate the turn on mechanism of the probe via ICT effect. Finally, a zebrafish larvae imaging experiment reveals that TPNF displayed a significant signal change when treated with FA in vivo. These results indicated that TPNF is a promising tool in more biomedical researches. [ABSTRACT FROM AUTHOR]

• A robust strategy for probe design with dual-quenching groups in one probe. • The strategy has been applied for designing HOCl fluorescent probe successfully. • The strategy can both enhance the probe's sensitivity and selectivity significantly. • The detection limit for HOCl is as low as 3.5 nM. • Two-photon probe has been used to detect HOCl in living cells and kidney tissues. We report herein fluorescent probes equipped with dual-quenching groups exhibiting superior sensitivity than probes with mono-quenching groups. Importantly, with this strategy, the probe with dual-quenching groups react with HOCl through two distinct reaction mechanisms, which reduce the plausible side reactions with other competing analytes and enhance the probe's selectivity. As a proof-of-concept study, we designed and synthesized a probe with dual-quenching groups DQ-HOCl to detect HOCl, which is one of the most important ROS and linked with a number of diseases. In addition, two control probes with mono-quenching groups, MQ-HOCl-1 and MQ-HOCl-2 , were also synthesized for comparison purpose. Fluorescent assays demonstrated that DQ-HOCl indeed shows ultra-high sensitivity and selectivity compared with probes with mono-quenching groups. Furthermore, the probe has been successfully utilized to imaging exogenous/endogenous HOCl in living cells. Moreover, DQ-HOCl was applied to visualize HOCl in kidney tissues from rat due to the increased penetration depth and lower tissue autofluorescence from the nature of two-photon probes. [ABSTRACT FROM AUTHOR]