Water-soluble naphthalimide-based 'Pourbaix sensors': pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer - ANR - Agence nationale de la recherche Accéder directement au contenu
Article Dans Une Revue New Journal of Chemistry Année : 2016

Water-soluble naphthalimide-based 'Pourbaix sensors': pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer

Résumé

Two novel naphthalimide-based 'Pourbaix sensors' for redox potential and pH were designed based on a 'fluorophore–spacer 1 –receptor–spacer 2 –electron-donor' configuration. The synthesised molecular logic gates consist of an alkylated 1,8-naphthalimide fluorophore connected to a tertiary amine by a flexible ethylene spacer to a ferrocene moiety via a methylene spacer. The UV-visible absorption and steady state fluorescent properties were examined in methanol and 1 : 1 (v/v) methanol/water. The spectroscopic properties are modulated by internal charge transfer (ICT) and photoinduced electron transfer (PET) mechanisms. A log b H + of 9.2 and 8.7 were determined in 1 : 1 (v/v) methanol/water for the methylated 1 and butylated 2 compounds, respectively. An apparent log b Fe 3+ of 4.2 was determined in 1 : 1 (v/v) methanol/ water at pH 4. Time-resolved spectroscopic studies elucidated the stimulus-modulated photoinduced electron transfer pathways. In the oxidised and protonated state, 1 exhibits a single fluorescence lifetime of 8.5 ns, while an efficient photoinduced electron transfer characterised by a time constant of 20 ps is revealed by femtosecond transient absorption spectroscopy in the absence of a perturbing stimulus.
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hal-01426556 , version 1 (04-01-2017)

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Alex D. Johnson, Kyle A. Paterson, Jake C. Spiteri, Sergey A. Denisov, Gediminas Jonusauskas, et al.. Water-soluble naphthalimide-based 'Pourbaix sensors': pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer. New Journal of Chemistry, 2016, 40 (12), pp.9917 - 9922. ⟨10.1039/C6NJ02023B⟩. ⟨hal-01426556⟩
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