Anthrone-spirolactam and quinoline hybrid based sensor for selective fluorescent detection of Fe3+ ions |
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Authors: | Ratanamala S Darole Denzil Britto Christopher Leslee Anagh Mukherjee Rajesh G Gonnade Sekar Karuppannan Beeran Senthilkumar |
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Institution: | 1. Organic Chemistry Division, CSIR – National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008 India;2. Department of Science and Humanities, Anna University – University College of Engineering, Dindigul, 624622 India;3. Physical/Materials Chemistry, CSIR – National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008 India
Academy of Scientific and Innovative Research, Ghaziabad, 201002 India;4. Center for Materials Characterization, CSIR – National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008 India
Academy of Scientific and Innovative Research, Ghaziabad, 201002 India |
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Abstract: | The synthesis of a novel, and highly selective Fe3+ ion sensor based on anthrone-spirolactam and its quinoline hybrid ligand is reported. The designed ligand displayed selective detection of Fe3+ ions with enhanced fluorescence emission. The complexation of Fe3+ ion led to a red shift of 32 nm from 420 nm to 452 nm, and a several fold increase in intensity with fluorescent green emission. The complexation (detection) of Fe3+ ions with ligand resulted in chelation enhanced fluorescence and intramolecular charge transfer through the inhibition of C=N isomerization. This hybrid sensor shows high sensitivity and selectivity, spontaneous response, and works on a wide pH range a minimum detection limit of 6.83 × 10?8 M. Importantly, the sensor works through the fluorescence turn-on mechanism that overcomes the paramagnetic effect of Fe3+ ions. The binding mechanism between the ligand and the Fe3+ ions was established from the Job's plot method, optical studies, Fourier transfor infrared spectroscopy, NMR titration, fluorescence life-time studies, and density functional theory optimization. The sensor displayed excellent results in the quantification of Fe3+ ions from real water samples. Furthermore, due to its biocompatibility nature, fluorescent spotting of Fe3+ ions in live cells revealed its bioimaging applications. |
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Keywords: | anthrone-spirolactam-quinoline cell imaging fluorescence intramolecular charge transfer iron |
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