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    Perylene Bisimide Aggregates as Probes for Subnanomolar Discrimination of Aromatic Biogenic Amines

    Year: 2019

    Journal: ACS Appl. Mater. Interfaces, Volume 11, 1-May, page 17079–17089

    Authors: Bettini, Simona; Syrgiannis, Zois; Pagano, Rosanna; Dordevic, Luka; Salvatore, Luca; Prato, Maurizio; Giancane, Gabriele; Valli, Ludovico

    Organizations: FutureInResearch APQ Ricerca Regione Puglia; PRIN 2017Ministry of Education, Universities and Research (MIUR)Research Projects of National Relevance (PRIN) [2017PBXPN4_003]

    Keywords: biogenic amines; perylene bisimides; fluorescence spectroscopy; pi-pi stacking; surface plasmon resonance; layer-by-layer technique; DFT calculations

    Perylene bisimide 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 pi-pi 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 between PBI aggregates and biogenic amines was exploited in order to discriminate aromatic amines down to subnanomolar concentrations by observing PBI fluorescence variations in the presence of various amines and at different concentrations. The experimental findings were corroborated by density functional theory 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. 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 the vapor phase and even if mixed with other aromatic amines.
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