Spectroscopic and Computational Study of a Naphthalene Derivative as Colorimetric and Fluorescent Sensor for Bioactive A
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SHORT COMMUNICATION
Spectroscopic and Computational Study of a Naphthalene Derivative as Colorimetric and Fluorescent Sensor for Bioactive Anions Darshna Sharma & Suban K. Sahoo & Rati Kanta Bera & Raj Kamal
Received: 26 October 2012 / Accepted: 24 February 2013 # Springer Science+Business Media New York 2013
Abstract The anion recognition property of a naphthalene based receptor (L) was investigated by naked-eye, UV-Vis, fluorescence, 1H NMR and computational methods. The receptor L showed fluoride selective naked-eye detectable colorimetric and UV-Vis spectral changes over other tested anions due to the formation of hydrogen bonding complex in 1:1 stoichiometry and/or deprotonation between fluoride and the receptor. Interestingly, the fluorescence of L was quenched by fluoride but enhanced by acetate. Keywords Anion recognition . Colorimetric and fluorescent sensor . Fluoride . Acetate . DFT
Introduction Anion recognition continues to be a major research goal for many supramolecular chemistry groups around the world. This is because anions play crucial role in a wide range of biological phenomena, chemical and environmental processes [1–6]. Anions are roughly present in 70 % of all enzymatic sites, which play essentials roles in many proteins and are critical for the manipulation and storage of genetic information [7]. It is also D. Sharma : S. K. Sahoo (*) Department of Applied Chemistry, S.V. National Institute of Technology (SVNIT), Surat, Gujrat, India e-mail: [email protected]
essential in the formation of majority of enzymesubstrate and enzyme-cofactor complexes as well as in the interactions of proteins with DNA or RNA. Among the different bio-active anions, fluoride and acetate are of prime importance. Acetate acts as a critical component in numerous metabolic processes [8, 9]. On the other hand, interest in the detection and recognition of fluoride ion is because of its significant role in dental caries, clinical treatment for osteoporosis, toxicity resulting from it’s over accumulation in the bone, and association with hydrolysis of the nerve gas sarin [10–12]. Because of the advancement in the supramolecular concepts on host-guest chemistry, numbers of suitable receptors have been developed for the selective encapsulation and sensing the biologically important anions for the qualitative and quantitative determination [13–16]. Particularly, the sensing of anion through the naked-eye (colorimetric), fluorescent and/or electrochemistry responses have attracted considerable attention. In this communication, we have introduced a simple and easy to prepare anion sensor L by combining 2-hydroxy-1naphthaldehyde with 2-aminophenol. Addition of one equivalent of F−, AcO− and H2PO4− anions to L solution in acetonitrile, naked-eye detectable color changes was observed from yellow to orange. Importantly, spectroscopic results reveal that the sensor L showed fluoride selective behavior in the presence of other competitive anions. The experimental evidences were well supported by theoretically estimated
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