Synthesis and characterization of bent fluorine-containing donor–π-acceptor molecules as intense luminophores with large Stokes shifts

Abstract

Herein, we prepared novel bent fluorine-containing donor–π-acceptor (D–π-A) molecules from commercially available octafluorocyclopentene using a facile two-step procedure, revealing that the above molecules absorb UV-light and exhibit yellow photoluminescence (PL) with high PL efficiencies (Φ_PL) in solution. The corresponding Stokes shifts exceeded 10 000 cm⁻¹, and the maximum PL wavelength (λ_PL) strongly depended on solvent polarity or intermolecular interactions in the solid state. On the basis of a Lippert–Mataga plot, PL was confidently assigned to radiative relaxation from an intramolecular charge-transfer excited state. Moreover, the synthesized luminophores showed intense PL even in the crystalline state and exhibited alkoxy chain length-dependent PL behavior (e.g., high Φ_PL, λ_PL = 486–540 nm).