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Donor-acceptor (D-A) diaryl maleimides have received widespread attention due to their outstanding aggregation-enhanced emissive (AEE) properties. Herein, we report a novel rectangular D-A conjugated macrocyclic tetramaleimide with two phenyl and two 2,7-pyrene moieties as the sidewalls, while the maleimides as four corner linkers via dynamic and reversible Perkin reactions under thermodynamic control. Due to the sensitive D-A conjugation effects resulted from the multipole moments by four maleimides, such unique macrocycle exhibits unusual solvatochromic luminescent properties with a typical D-A charge transfer (CT) emission feature in the polar solvents, but pyrene-like emission characteristics in the nonpolar solvents regardless of the concentrations. A novel rectangular D-A conjugated macrocyclic tetramaleimide has been synthesized via dynamic and reversible Perkin reactions, which exhibits unusual solvatochromic luminescent properties. [Display omitted] • A facile synthetic pathway for rectangular D-A conjugated macrocyclic maleimides have been developed. • Dynamic covalent Perkin reactions have been demostrated to be an efficient synthetic pathway for macrocyclic maleimides. • The obtained macrocyclic maleimides exhibit unexpected solvatochromic luminescent properties. • The obtained macrocyclic maleimides exhibit a typical D-A charge transfer (CT) emission feature in the polar solvents. • The obtained macrocyclic maleimides exhibit pyrene-like emssions in carbon tetrachloride. [ABSTRACT FROM AUTHOR]