A new fluorescent sensor was developed, in which pyrene is conjugated to calix[4]triazolium via an ester linker, and its ability to bind anions was investigated. Interestingly, addition of HSO4- to Py-CT4 resulted in increased fluorescence, but other anions had little effect. This phenomenon is attributed to the formation of a 1:1 stoichiometric Py-CT4-HSO4- complex that interferes with the photoinduced electron transfer (PET) process. The selectivity of Py-CT4 for HSO4− is the result of appropriate spatial complementarity to, and hydrogen bond interaction with, HSO4−. The binding mode and fluorescence changes caused by the PET process can be explained well by density functional theory (DFT) calculations.

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