Host-Guest Complexation Affects Perylene-Based Dye Aggregation

Abstract

A fluorescent perylene-based dye (PDI) was designed with two aromatic moieties at the imide position of the perylene core. The dye displayed contrasting behavior with water-soluble macrocycles. Cucurbit[n]urils (CB7 and CB8) reduced the self-aggregation of the dye molecules, while sulfonatocalixarenes (SCX4 and SCX5) and sulfonato-β-cyclodextrin (S-β-CD) resulted in a complexation-enhanced aggregation. In regard to potential applications, the CB8•PDI complex served as an excellent reporter pair inside cells to detect the uptake of neurotransmitters by fluorescence.