Click-derived Macrocycles For Anion/Cation Recognition

Anions are playing a more and more important role in biological chemistry, so the rapid and efficient detection of the anions and cations become more and more challenging to the scientists. Because of the hydrogen bond of the C-H with anions in the 5th C of the triazole and electron-rich in the 3th N which can bind to cations,make the triazole become a good receptor to cations and anions. So the triazole often be used in the design and Synthesis of the sensors, and in the other side in consideration of macrocyclic can matching well with the anions and cations with the cavity which can adjust easily, and good sensitivity and selectivity to ions compared to the non-macrocyclic, so this article synthesised a series of macrocyclic through “click” chemistry, and detected the bind ability to cations and anions with electro-chemistry?UV absorption?fluorescence emission spectrum and 1H NMR titration.1. based on Ferrocene and naphthalene Respectively as the single for electrochemistry and fluorescence detect, a macrocyclic which contain four triazoles has been designed and Synthesised, and detected the recognition ability for anions with electrochemical properties test, ultraviolet-visible absorption spectra, fluorescence emission spectrum titration and 1HNMR titration. The 1HNMR titration indicated that the compound 1 interacts with anion by the C – H of triazoles, and the proton of the triazole shift 1.19 ppm to the low-field; and the electrochemical properties test show that the potential changed 70 mV, 100 mV Respectively when complex with Pi- and F-,which indicated that it can alternatively recognition of Piand F-.2. A new anion sensor based on the triazole with the Anthracene as the fluorophore was designed and Synthesised, and we found that through the rich electronics group N, O in the amido bond and the N in the triazole, provide well bind site for selectivity recognition of cations. So when we research the recognition property of the ligand to alkali metals, alkaline earth metals and transition metals cations, it reflect fluorescence quenching to the Cu²⁺, the fluorescence titration experiment show that when titration 10 eq of Cu²⁺, the fluorescence intensity of the ligand decreased to 50 from 700, and saturated. And showed no obvious recognition to other cations.3. Designed and Synthesised a series of orbicular ligands which contains acridine, Anthracene and naphthalene as the fluorophore respectively, detected the recognition ability for anions with ultraviolet-visible absorption spectra and fluorescence emission spectrum titration, and indicated that the orbicular ligand contains acridine shows that the fluorescence has been enhanced to the Hg²⁺ and debilitated to Cu²⁺.but the host of Anthracene and naphthalene both reflect fluorescence reduce to Cu²⁺ and Hg²⁺.