This article describes the synthesis of naphthofuran-based probes NF, NNF, and BNFvia a multiple-step synthetic approach and their characterization using standard spectroscopic techniques such as FT-IR, 1H NMR, 13C-NMR and HR-MS spectrometry. The inclusion complex (IC-NNF) has also been synthesized by encapsulating the NNF molecule into the hydrophobic cavity of β-CD. The chemosensing properties of all these probes have been investigated using UV-visible and fluorescence spectroscopy. However, all these probes could interact with metal ions, only NNF showed chemoselectivity towards Pb2+ detection. The limit of detection (LOD) and binding constant were calculated to be 1.47 µM and 7.38 ⅹ 1010 M−2 for NNF using the Stern-Volmer and Bensi-Hiderland plots, respectively. Further studies revealed that the –NO2 group and furan oxygen in NNF simultaneously interacted with the empty orbital of Pb2+ to produce the "turn-on" spectra.