Temperature-Dependent Self-Assembly Remodeling by a Polyether Perylene Diimide in Water

We report a novel Perylene diimide (PDI) bearing polyether side chains that displays reversible, temperature depended remodeling of two spectroscopically distinct self-associated forms. We describe the synthesis of this PDI (TEL-045) and its self-association behavior in solution as determined by UV/Vis, fluorescence, and resonant light scattering spectral analysis. TEL-045 forms monomeric, emissive species in solution in organic solvents. In aqueous solution, TEL-045 undergoes self-association to produce a non-emissive state. As the temperature of aqueous solutions of TEL-045 are increased, the degree of self-association increases, leading to LCST behavior and a new type of self-associated, emissive species. This reversible, temperature-dependent switching between H- and J-type self-association of this simple, a non-chromophore-modified PDI leads to marked changes in fluorescence enabling temperature-sensing and other applications.