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Title: | Water-soluble naphthalimide-based ‘Pourbaix sensors’ : pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer |
Authors: | Johnson, Alex D. Paterson, Kyle A. Spiteri, Jake C. Denisov, Sergey A. Jonusauskas, Gediminas Tron, Arnaud McClenaghan, Nathan D. Magri, David C. |
Keywords: | Electron transport Hydrogen-ion concentration Ethylene Ferrocene Methanol |
Issue Date: | 2016 |
Publisher: | Royal Society of Chemistry |
Citation: | Johnson, A. D., Paterson, K. A., Spiteri, J. C., Denisov, S. A., Jonusauskas, G., Tron, A., ... & Magri, D. C. (2016). Water-soluble naphthalimide-based ‘Pourbaix sensors’: pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer. New Journal of Chemistry, 40(12), 9917-9922. |
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 bH+ 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 bFe3+ 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. |
URI: | https://www.um.edu.mt/library/oar/handle/123456789/70755 |
Appears in Collections: | Scholarly Works - FacSciChe |
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Water_soluble_naphthalimide_based_pourbaix_sensors.pdf Restricted Access | 3.16 MB | Adobe PDF | View/Open Request a copy |
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