Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes

We report the facile, metal-free convergent synthesis and the characterization of novel quinacridone dyes in which two triptycene units end-cap and sterically confine the quinacridone chromophore. A precise comparison of the confined dyes with their known homologues reveals that the reduction of p-p interactions in triptycene-fused quinacridone dyes compared to classical quinacridone results not only in an increase of solubility and processability but also in an enhancement of fluorescence quantum yield and photostability in the solid state.

Automated summary

We report a facile, metal-free convergent synthesis method and characterization of novel quinacridone dyes with two triptycene units that function as end-caps and steric confinements for the quinacridone chromophore. A precise comparison between the confined dyes and known homologues reveals that the reduction of p-p interactions in triptycene-fused quinacridone dyes, compared to classical quinacridone, leads to increased solubility, processability, fluorescence quantum yield, and photostability in the solid state.