Perylene Diimide-Based Ionene and Zwitterionic Polymers: Synthesis and Solution Photophysical Properties

A series of perylene diimide (PDI)-containing ionene and zwitterionic polymers were prepared by the Menschuktin reaction and by nucleophilic ring-opening of a novel bis-sultone monomer. PDI derivatives containing tertiary amine moieties at the imide position, and bromides or phenyl groups within the aromatic core, provided sites for polymerization and imparted solubility during the polymerization, respectively. The solution photophysical behavior of the polymers was studied by UV–vis and photoluminescence spectroscopy as a function of PDI incorporation and cationic/zwitterionic functionality, resulting in the observation of tunable solution spectral features induced by core functionality and/or interzwitterion interactions. This new PDI-based polymer platform affords opportunities to modulate conjugation and charge density within the polymers and examine the effects of cationic vs zwitterionic groups on the resultant optoelectronic properties.