Abstract
A molecular clip combining a doubly substituted fluorescent anion–π donor probe and two flexible arms bearing H-bond motifs constitutes a new generation of anion receptors. Five simultaneous non-covalent interactions are highlighted by theoretical complexation studies with five different anions. A large range of analytical techniques (electrospray-tandem mass spectrometry, NMR, UV-visible, steady-state and time-resolved fluorescence) were deployed to evaluate the stoichiometry and association constants with the selected anions. The photophysical and anion–π donor properties of the tetrazine ring allowed fine characterization of the binding properties of the ligand. Based on previously published results, an anti-cooperativity effect in non-covalent interactions was demonstrated.
Highlights
Non-covalent interactions have been widely used in the elaboration of new molecular organic architectures
Prior to the examination of the complexation properties of the new ligand synthesized, we evaluated the binding and conformational preferences of our new ligand with ve different anions through density functional theory (DFT) calculation using Gaussian 09 so ware
Optimized geometries are detailed in the Electronic supplementary information (ESI) (ESI pp.7–20).† Illustrations of the electronic and binding properties of the complexes were assessed by calculating the Electrostatic Potentials Surfaces (ESP) using the Gaussview so ware from optimized structures using a ne grid for total density and a medium grid for ESP
Summary
Non-covalent interactions have been widely used in the elaboration of new molecular organic architectures. A shortening of H–X distances is observed for Ha and Hd that are close to the bis(tri uoromethyl) phenyl group, compared to Hb and Hc. Distances between anion and centroid of tetrazine ring were determined (Table 3, entry 9).[30] These distances are close for ClÀ (3.31 A) and BrÀ (3.42 A) but markedly increased for IÀ (3.79 A).
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