Two metal-free tetra(aryl)porphyrin derivatives modified by one and four N,N-bis(2-pyridylmethyl)amino group(s), namely porphyrin-1-DPA (1) and porphyrin-4-DPA (2) respectively, have been designed, synthesized, and characterized. Binding with Pb2+ induces a significant change in their solution color and in the ratio of two absorption/fluorescence signal peaks, rendering them the first example of porphyrin-based triple-signal optical sensors for Pb2+. Their dual-mode Cu2+-selective sensing properties via either the porphyrin fluorescence ON–OFF mechanism or metal displacement from the 1–Pb2+ complex that results in a triple-signal change clearly reveals their potential application as excellent and versatile sensors.
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Organic & Biomolecular Chemistry
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