The　synthesis,　characterization,　and　properties　of　phthalimide-fused　phenanthrenone　(PIP)　and　its　dicyano　derivative　(PIPCN)　are　reported　in　this　study.　A　three-step　synthetic　route　was　established　for　the　preparation　of　PIP.　Single-crystal　X-ray　diffraction　revealed　PIP＇s　rigid　pi-conjugated　framework　and　significant　intermolecular　interactions.　Systematic　UV-vis　absorption　spectra　and　DFT　calculations　demonstrated　that　the　dicyano　group　in　PIPCN　enhances　intramolecular　charge　transfer　effects,　resulting　in　lower　LUMO　energy　levels　compared　to　classical　imide　units　such　as　naphthalene　diimide　(NDI)　and　perylene　diimide　(PDI).　Furthermore,　Z-scan　experiments　highlighted　PIPCN＇s　pronounced　third-order　nonlinear　optical　properties.　These　findings　demonstrate　that　PIP　and　PIPCN　are　promising　candidates　for　applications　in　organic　electronics　and　nonlinear　optical　materials.