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Perylene Bisimide (PBI) derivatives show peculiar physical chemical features, such as a highly conjugated system, high extinction coefficients and elevated fluorescence quantum yields, making them suitable for the development of optical sensors of compounds of interest. In particular, they are characterized by the tendency to aggregate into π-π stacked supramolecular structures. In this contribution, the behavior of the PBI derivative N,N'-bis(2-(trimethylammonium)ethylene)perylene bisimide dichloride was investigated both in aqueous solution and on solid support. The electronic communication among PBI aggregates and biogenic amines was exploited in order to discriminate aromatic amines down to sub-nanomolar concentrations by observing PBI fluorescence variations in presence of various amines and at different concentrations. The experimental findings were corroborated by DFT calculations. In particular, phenylethylamine and tyramine were demonstrated to be selectively detected down to 10-10 M concentration. Then, in order to develop a Surface Plasmon Resonance (SPR) device, PBI was deposited onto a SPR support by means of the layer-by-layer method. The PBI was deposited in the aggregated form and was demonstrated to preserve the capability to discriminate, selectively and with an outstanding analytical sensitivity, tyramine in vapor phase and even if mixed with other aromatic amines.
This article was published in the following journal.
Name: ACS applied materials & interfaces
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