Síntesis y estudio de receptores dipodales de aniones mediante enlace de halógeno e hidrógenoprocesos de reconocimiento y formación de polímeros supramoleculares

Abstract

The main objective of this PhD is the synthesis and the comparative study of new dipodal receptors in the anion recognition process by hydrogen or halogen bonding interactions, as well as a detailed study of the anion binding mode. The 1,2,3-triazolium ring was used as anion binging site. In order to study how affects the incorporation of substituents with different electronic characteristics in the anion recognition process, electron-donor, electron-acceptor and neutral substituents have been incorporated in the 4-position of the 1,2,3-triazolium ring. The incorporation of bridges with different sizes: naphthalene, phenol and binaphthol have allowed to determine how the size of the cavity affects in the anion recognition process. During this PhD, we have paid special attention to the binding mode between the receptors and anions. In addition to the more obvious halogen or hydrogen bond interactions, other non-covalent interactions have been detected, among which we highlight: * Csp2-H····A- hydrogen bonds interactions. * Csp3-H···A- interactions * Anion-Pi interactions. Finally, we have demonstrated one of the initial hypotheses of this PhD, which is that polydentate halogen-bond receptors can form supramolecular polymers by the formation of consecutive intermolecular complexes through monomer-anion interactions by halogen bond, preferably to the recognition by a single receptor. The molecules synthesized, have been characterized and studied by mass spectrometry, melting point, 1H-NMR, 13C-NMR, Fluorescence, UV-Vis and Electrochemical. In the case of supramolecular polymers, we have also been used Electron Microscopy, X-Ray Diffraction, Dynamic Light Scattering and Circular Dichroism among others.