Abstract
A fluorescent and colorimetric molecular probe containing phenol groups has been designed and synthesized. The anion binding ability was evaluated for biolgically important anions (F−, Cl−, Br−, I−, AcO− and H2PO4−) by theoretical investigation, UV-Vis and fluorescence spectroscopy and 1H-NMR titration experiments. Results indicated the probe showed strong binding ability for H2PO4− without the interference of other anions tested and the interaction process was accompanied by color changes. Theoretical investigation analysis revealed that intramolecular hydrogen bonds existed in the structure of the probe and the roles of molecular frontier orbitals in molecular interplay were determined.
Highlights
In recent years, increasing attention in the field of host-guest chemistry has been devoted to the fast development of anion recognition system [1–11]
In order to make good use of fluorescent and colorimetric dual sensing molecules for the detection of H2PO4−, here we reported a phenanthroline derivative, 2,9-di((2',3'-diaza-4'-(2′′-hydroxy-5′′nitrophenyl)-1',3'-butadiene)-1,10-phenanthroline (1, Scheme 1), which consists of a phenanthroline system and a nitro group as well as hydroxyl groups as a dual responsive fluorescent and colorimetric probe
H2PO4− was increased, the absorption intensity at 340 nm gradually decreased and two new absorption peaks appeared at 400 nm and 475 nm, which was accompanied by a visual color change from light yellow to orange (Figure 2)
Summary
In recent years, increasing attention in the field of host-guest chemistry has been devoted to the fast development of anion recognition system [1–11]. The development of fluorescent and colorimetric probes for anions is timely and an area of current interest. Molecules 2013, 18 the focus has been mainly on the design of a receptor which has the ability to recognize and bind biological anions. This approach suffers from shortcomings such as the high cost of synthesis and the loss of the real-time response. In order to make good use of fluorescent and colorimetric dual sensing molecules for the detection of H2PO4−, here we reported a phenanthroline derivative, 2,9-di((2',3'-diaza-4'-(2′′-hydroxy-5′′nitrophenyl)-1',3'-butadiene)-1,10-phenanthroline (1, Scheme 1), which consists of a phenanthroline system and a nitro group as well as hydroxyl groups as a dual responsive fluorescent and colorimetric probe.
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