Modular Synthesis of Phenazine-Based Aggregation-Induced Emission Materials

The facile condensation of bis(triphenylethylene)-functionalized <i>ortho</i>-phenylenediamine with <i>ortho</i>-quinones gives phenazine-based luminogens in high yield. Fluorescence studies demonstrate that each of the four new phenazine derivatives displays aggregation-induced emission (AIE) behavior in THF solutions containing ≥60% water. The sizes and structures of aggregates have been investigated further by dynamic light scattering, confocal microscopy, and scanning electron microscopy, each showing a decrease in the size of roughly spherical particles with increasing percentage of water.