Demonstration of bidirectional photoinduced electron transfer (PET) sensing in 4-amino-1,8-naphthalimide based thiourea anion sensors
Citation:
Emma B. Veale, Gillian M. Tocci, Frederick M. Pfeffer, Paul E. Kruger, and Thorfinnur Gunnlaugsson, Demonstration of bidirectional photoinduced electron transfer (PET) sensing in 4-amino-1,8-naphthalimide based thiourea anion sensors, Organic & Biomolecular Chemistry, 7, 17, 2009, 3447-3454Download Item:
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Abstract:
The thiourea based 4-amino-1,8-naphthalimide molecules 1-5 were designed as fluorescent anion sensors and their photophysical properties investigated upon recognition of biologically relevant anions such as acetate, dihydrogen phosphate and fluoride in DMSO. Synthesised in a single step from their respective aniline precursors, 6-9, these molecules were designed on the fluorophore-spacer-receptor principle, where in the case of sensors 1-3 the thiourea anion recognition moieties were connected to the fluorophore via the 4-amino moiety, while sensors 4 and 5 had the thiourea moieties connected to the 'imide' via a CH2 spacer. The current study showed that 1-5 operated as photoinduced electron transfer (PET) sensors, as no significant changes were observed in their absorption spectra, while their fluorescence emissions were quenched upon recognition of ions such as AcO(-), H2PO4(-) and F(-), which demonstrates that bidirectional PET sensing occurs in such naphthalimide based anion sensors.
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Irish Research Council for Science and Engineering Technology (IRCSET)
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http://people.tcd.ie/gunnlauthttp://people.tcd.ie/krugerp
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PUBLISHED
Author: GUNNLAUGSSON, THORFINNUR; KRUGER, PAUL
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Organic & Biomolecular Chemistry7
17
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