SPITERI, Jake; JOHNSON, Alex; DENISOV, Sergey; JONUSAUSKAS, Gediminas; MCCLENAGHAN, Nathan; MAGRI, David

doi:10.1016/j.dyepig.2018.04.060

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SPITERI, Jake
Department of Chemistry [Msida]

JOHNSON, Alex
Department of Chemistry [Msida]

DENISOV, Sergey
Institut des Sciences Moléculaires [ISM]

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Dyes and Pigments. 2018, vol. 157, p. 278-283

Elsevier

Résumé en anglais

A novel fluorescent molecular logic gate 1 is demonstrated as a two-input AND logic gate for the detection of acidity and oxidizability. Designed according to an electron-donor–spacer–fluorophore–spacer–receptor' format, the modules are represented by ferrocene as the electron donor, 1,8-naphthalimide as the fluorophore and piper-azine as the proton receptor. In the presence of elevated concentrations of H + and Fe 3+ , the molecule switches 'on' emitting at λ max = 530 nm with Φ f = 0.060 at 10 −4 M H + and 50 μM Fe 3+. The H + binding and apparent Fe 3+ binding constants determined by fluorimetric titrations in 1:1 (v/v) methanol/water are log β H+ = 8.1 and log β Fe3+ = 4.7. Modulation of the fluorescence output results from controlling competing photoinduced electron transfer (PET) at the ferrocene end and internal charge transfer (ICT) at the piperazine end. Time-resolved fluorescence spectroscopy reveals a single fluorescent lifetime of 5.8 ns, while from absorption transient spec-troscopy a remarkable fast decay signal < 2 ps is observed. Comparison is made with methylpiperazine 2 and piperazine fluorescent pH indicator 3 as model compounds.< Réduire

Mots clés en anglais

Naphthalimide

Ferrocene

Photoinduced electron transfer

Pourbaix sensor

Molecular logic gate

Fluorescence

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A fluorescent AND logic gate based on a ferrocene-naphthalimide-piperazine format responsive to acidity and oxidizability

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