A novel pyrene-pyridyl conjugated oligomer (OPP-OMe) was conveniently prepared by one-pot Sonogashira coupling. Intriguingly, it was found that introducing only one methoxy moiety at the 4-pyridyl position can be sufficient for creating an oligomer-based ultrafine reactive fluorescent nanoprobe, i.e., OPP-OMe NPs (ca. 2.5 nm in diameter). Spectral analyses and elucidation of the intermediate structure revealed that the methoxy triggered-oxidation, together with nanoaggregation of OPP-OMe NPs, results in rapid, specific and supersensitive sensing of hypochlorite (LOD, 0.3 nM, S/N = 3).