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Issue 12, 2016
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Water-soluble naphthalimide-based ‘Pourbaix sensors’: pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer

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Abstract

Two novel naphthalimide-based ‘Pourbaix sensors’ for redox potential and pH were designed based on a ‘fluorophore–spacer1–receptor–spacer2–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 βH+ 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 βFe3+ 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.

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

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Publication details

The article was received on 28 Jun 2016, accepted on 22 Aug 2016 and first published on 30 Aug 2016


Article type: Paper
DOI: 10.1039/C6NJ02023B
Citation: New J. Chem., 2016,40, 9917-9922
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    Water-soluble naphthalimide-based ‘Pourbaix sensors’: pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer

    A. D. Johnson, K. A. Paterson, J. C. Spiteri, S. A. Denisov, G. Jonusauskas, A. Tron, N. D. McClenaghan and D. C. Magri, New J. Chem., 2016, 40, 9917
    DOI: 10.1039/C6NJ02023B

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