Abstract
New phenanthroline derivatives (1, 2, 3, 4) containing phenol groups have been synthesized and optimized. The nano-material of compound 2 was also developed. Their binding properties were evaluated for various biological anions (F(-), Cl(-), Br(-), I(-), AcO(-) and H(2)PO(4)(-)) by theoretical investigation, UV-vis, fluorescence, (1)HNMR titration experiments and these compounds all showed strong binding ability for AcO(-) without the interference of other anions tested. The anion binding ability could be regularized by electron push-pull properties of the ortho- or para- substituent on benzene. Theoretical investigation analysis revealed the effect of intramolecular hydrogen bond existed between -OH and other atoms in the structure of these compounds.
Highlights
The growing attention on anion recognition has attracted more and more chemists due to important roles of anions in biological, chemical and environmental processes.[1,2,3,4,5,6,7,8,9,10] The anion recognition by artificial receptors is an area of ever increasing research activity.[11]
Some compounds have been reported that they can bind acetate ion with high affnity and the acidity of the hydrogen-bond donor can be enhanced if the intramolecular hydrogen bonding exists in artificial receptor.[23,24,25]
Four colorimetric anion sensors involving phenanthroline and phenol groups were successfully synthesized and optimized. They interacted with anions by hydrogen bond and showed the strong binding ability for AcO– without the interference of other anions studied
Summary
The growing attention on anion recognition has attracted more and more chemists due to important roles of anions in biological, chemical and environmental processes.[1,2,3,4,5,6,7,8,9,10] The anion recognition by artificial receptors is an area of ever increasing research activity.[11]. The binding units are often composed of amide,[17] urea / thiourea and pyrrole owing to their binding ability performing as hydrogen donors.[18,19,20,21] Anions are ubiquitous throughout biological systems. Some anions such as fluoride, chloride, bromide, acetate, dihyphosphate, and etc play important roles in a range of biological process and are implicated in many disease states.[22] Especially, acetate anion displays crucial behavior and is the important component of numerous metabolic processes. Results indicate that four compounds show the highest binding ability for acetate ion among anions tested These observations suggest that an oxy-anion bonding interlocked host binding domain, in combination with increased inter-component preorganisation, are requisite design features for a potent anion receptor
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