Synthesis and Characterization of Bola‐Amphiphilic Porphyrin‐Perylenebisimide Architectures

We report on the synthesis and characterization of a family of three water‐soluble bola‐amphiphilic zinc‐porphyrin‐perylenebisimide triads containing oligo carboxylic‐acid capped Newkome dendrons in the periphery. Variations of the perylenebisimide (PBI) core geometry and dendron size (G1 and G2 dendrons with 3‐ and 9‐carboxylic acid groups respectively) allow for tuning the supramolecular aggregation behavior with respect to variation of the molecular architecture. The triads show good solubility in basic aqueous media and aggregation to supramolecular assemblies. Theoretical investigations at the DFT level of theory accompanied by electrochemical measurements unravel the geometric and electronic structure of the amphiphiles. UV/Vis and fluorescence titrations with varying amounts of THF demonstrate disaggregation. We report the synthetic approach and the characterization of a family of highly water‐soluble porphyrin‐PBI donor‐acceptor amphiphiles by the utilization of oligo‐carboxylic acid capped Newkome dendrons. The amphiphiles form stable aggregates in basic aqueous solutions. The amphiphiles can be individualized by the addition of THF, which manifests itself, for example, in the reinstatement of fluorescence emission.