Department of Chemistry "Ugo Schiff", University of Florence, Via della Lastruccia, 3-13, 50019 Sesto Fiorentino, Italy.
Department of NEUROFARBA-Pharmaceutical and Nutraceutical section, and Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Florence, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy.
Molecules. 2020 Mar 17;25(6):1355. doi: 10.3390/molecules25061355.
Synthesis of the new scorpiand ligand L composed of a [9]aneN macrocyclic ring bearing a CHCHNHCH-anthracene tail is reported. L forms both cation (Zn) and anion (phosphate, benzoate) complexes. In addition, the zinc complexes of L bind these anions. The equilibrium constants for ligand protonation and complex formation were determined in 0.1 M NaCl aqueous solution at 298.1 ± 0.1 K by means of potentiometric (pH-metric) titrations. pH Controlled coordination/detachment of the ligand tail to Zn switch on and off the fluorescence emission from the anthracene fluorophore. Accordingly, L is able to sense Zn in the pH range 6-10 down to nM concentrations of the metal ion. L can efficiently sense Zn even in the presence of large excess of coordinating anions, such as cyanide, sulphide, phosphate and benzoate, despite their ability to bind the metal ion.
报告了一种新型的 scorpand 配体 L 的合成，它由一个带有 CHCHNHCH-蒽尾部的[9]aneN 大环组成。L 可以形成阳离子（Zn）和阴离子（磷酸盐、苯甲酸盐）配合物。此外，L 的锌配合物还可以结合这些阴离子。通过电位（pH 计）滴定法在 298.1 ± 0.1 K 的 0.1 M NaCl 水溶液中测定了配体质子化和配合物形成的平衡常数。通过控制 pH 值，可以使配体尾部与 Zn 的配位/解配位开关打开或关闭蒽荧光团的荧光发射。因此，L 能够在 pH 值为 6-10 的范围内检测到 nM 浓度的金属离子。即使在存在大量配位阴离子（如氰化物、硫离子、磷酸盐和苯甲酸盐）的情况下，L 也能够有效地检测 Zn，尽管它们能够与金属离子结合。
