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New pyrenyl mono- and disubstituted fluorene and carbazole derivatives were synthesized and investigated as blue-emitting materials. Most of the synthesized compounds were capable of forming glasses with glass transition temperatures up to 105 °C. The mono- and disubstituted compounds exhibited efficient emission in a diluted form with the peak wavelengths of 416 and 422 nm and quantum yields of 0.72 and 0.82, respectively. Photophysical properties of the compounds in dilute solutions and solid state were investigated experimentally and rationalized by density functional theory calculations. The calculations revealed a low energy barrier for intramolecular twisting in the ground and excited states. The electronic spectra of the compounds were dominated by an allowed “pyrene-like” S0 → S2 transition prevailing in nearly perpendicularly twisted molecular structures and competitive S0 → S1 transition becoming increasingly allowed for more planar conformers. The disubstituted compounds demonstrated a 3-fold e...