Langmuir–Blodgett films of perylene bisimide derivatives and fluorescent recognition of diamines

Fast, sensitive and selective detection of diamines in the vapor phase is of pivotal importance for air and food quality monitoring. In this work, an electron-poor fluorophore, perylene bisimide (PBI), was modified with hydrophilic residues at its bay positions, resulting in an amphiphilic derivative, PEBBO. Photophysical studies revealed that the compound shows a strong aggregation tendency in various solvents, but the aggregates could be highly fluorescent provided suitable solvents are used. Accordingly, a fluorescent film was constructed via utilization of the well-known Langmuir–Blodgett technique. Sensing performance studies revealed that the film as prepared is sensitive and selective to the presence of diamines in air. Specifically, (1) the experimental detection limit is lower than 0.016 g m−3 and the linear range of the analysis extends from 0.33 g m−3 to 8.20 g m−3 when ethylenediamine was adopted as an example analyte; (2) the presence of other amines and solvents shows little effect upon detection; (3) the response time is less than 5 s. Considering the importance of diamine sensing, the convenience of fluorescence techniques and the superiorities of the film and method as developed, it is believed that the present work is of great importance for promoting technical progress in diamine sensing.