Demonstration of bidirectional photoinduced electron transfer (PET) sensing in 4-amino-1,8-naphthalimide based thiourea anion sensors

被引:111
作者
Veale, Emma B. [1 ]
Tocci, Gillian M. [1 ]
Pfeffer, Frederick M. [2 ]
Kruger, Paul E. [1 ,3 ]
Gunnlaugsson, Thorfinnur [1 ]
机构
[1] Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
[2] Deakin Univ, Fac Sci & Technol, Sch Life & Environm Sci, Waurn Ponds, Vic 3217, Australia
[3] Univ Canterbury, Coll Sci, Dept Chem, Christchurch 8020, New Zealand
关键词
COLORIMETRIC NAKED-EYE; MODULAR APPROACH; FLUORESCENT SENSORS; HIGH SELECTIVITY; RECOGNITION; BINDING; RECEPTOR; DEPROTONATION; CHEMOSENSORS; LUMINESCENT;
D O I
10.1039/b907037k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:3447 / 3454
页数:8
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