Fine-Tuning the Electronic Properties of Azo Chromophore-Incorporated Perylene Bisimide Dyads.

Perylene bisimide (PBI) and azo-compounds are fascinating molecules with interesting optical properties. Here, we combine the two chromophores to prepare nonconjugated and conjugated stable azo-PBI dyes. The detailed structural characterization, comparison of properties, and solid-state self-assembly of the compounds are discussed. The incorporation of azo groups at the bay side of PBI led to significant changes in optical properties as compared to the model PBIs (M1 and M2). All new azo-PBIs showed photoinduced isomerization, which caused disaggregation and enhancement in fluorescence. The amine-incorporated azo-PBIs (3 and 6) reduced chloroauric acid into gold nanoparticles. The current study offers a simple synthetic strategy and comparison of the properties of conjugated and nonconjugated azo-PBIs, which could be useful in photoelectronic devices.