A novel 3-5-dichlorosalicylaldehyde Schiff base chemodosimeter (compound 1) for water is designed and synthesized, and it works based on a water-triggered reaction of a Schiff base. Addition of trace amounts of water into 1 in various organic solvents leads to a fluorescence turn-on response and a simultaneous dual-channel signal modulation (both in the fluorescence and absorption spectra). Especially, 1 is found to be an outstanding fluorescence enhancement water sensor in methanol with an extremely low detection limit of 22 ppm. Consequently this probe can be utilized to detect trace water in commercial methanol. The quantitative detection of a wide range of water content is enhanced in THF and acetonitrile (0-35% v/v for THF and 0-20% v/v for acetonitrile), where the fluorescence peak intensity is nearly proportional to the amount of water added. Moreover, 1 can be used for monitoring pH through a novel ON-OFF-ON type signal modulation both in fluorescence and absorption spectra within a wide pH detection range. Thus, the chemodosimeter can not only be utilized to monitor the intracellular pH fluctuations, but also to accomplish simultaneous in situ staining of the cytosol and acidic organelles in two different channels, respectively.
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