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• Donor–Acceptor Chalcone Containing Phenanthrene and Thiophene Moieties. • PhTPO would be useful to study the microenviromental polarity and evaluation of critical micelle concentrations of thestudied surfactants. • Reversible acidochromic behavior after addition of H 2 SO 4 /NaOH with a color change. • Optical sensing response towards H+, Co2+, Ni2+, Pb2+ and Cd2+ ions. • Anticancer activity for the free ligand and its solid complexes. Donor–Acceptor (D–π–A) chalcone containing phenanthrene and keto-thiophenly moieties, abbreviated as PhTPO , was synthesized and characterized. The solvatochromic effect was investigated in different solvents of various polarities. The absorption and fluorescence spectra have shown bathochromic shifts from non-polar to polar solvents due to intramolecular charge transfer interactions. The fluorescence characteristics (fluorescence intensity, fluorescence maxima, and energy) of PhTPO are highly sensitive to the polarity of the solvents compared to the corresponding absorption spectra. In addition, the inclusion characteristic of PhTPO in different organized assemblies was studied. The spectral changes suggested that PhTPO would be useful to study the microenviromental polarity and evaluation of critical micelle concentrations of the studied surfactants. Reversible acidochromic behavior was observed after addition of H 2 SO 4 /NaOH with a significant color change. Further, the optical sensing response towards H+, Co2+, Ni2+, Pb2+ and Cd2+ ions was investigated. Also, it responds well to the tested metal ions as reflected from the changes in both the absorption and emission spectra upon adding different concentrations of the metal salts. The solid complexes of PhTPO with Co2+, Ni2+, Pb2+ and Cd2+ were then synthesized and characterized. Depending on the magnetic moments results, the geometric structures were found to be octahedral and tetrahedral for paramagnetic Co2+, and Ni2+ complexes, respectively, while they are diamagnetic for Pb2+ and Cd2+ complexes. Moreover, the geometry of PhTPO and its complexes were confirmed by the density functional theory (DFT) using DMOL3 program. The binding affinity towards the epidermal growth factor receptor (EGFR) protein was also investigated by the Molecular Operating Environment (MOE) software. The anticancer activity was then evaluated against four different cell lines using MTT assay. The results suggest that the investigated PhTPO would be potential candidate for solvents polarity sensors, as a probe to characterize critical micelle concentrations of surfactants, and sensor for the studied metal ions and H+ proton. In addition, [ PhTPO Ni2+] and [ PhTPO Co2+] complexes are good candidate for further antitumor activities studies owing to their potent cytotoxic and anticancer activities compared to the Pb2+ and Cd2+ complexes. [Display omitted] [ABSTRACT FROM AUTHOR]