Abstract
In this work, we present the synthesis of a novel Zn-Salphen complex containing an allyl group, which was used as building block in the further preparation of a new family of functional terpolymers. These polymers were obtained through radical co-polymerization with methyl metacrylate (MMA) and n-butyl acrylate (nBuA) in different ratios. The supramolecular recognition behavior of each polymer was evaluated via potentiometric measurements against selected anions in aqueous media. Interestingly, this proof of concept study shows that these systems were selective against only fluoride (F−) or both, fluoride and acetate (OAc−), by tailoring the relative content of Zn-Salphen monomer, thus making them a promising starting point for modular design of chemical sensors through straightforward synthetic approaches.
Highlights
Zn-Salphen complexes are compounds that can be synthesized by the condensation of o-phenylene diamine and salicylaldehyde derivatives, which, after coordination with Zn(II), form a wide range of imine-based complexes showing interesting and useful chemical features
The possibility for further intermolecular coordination between the Zn center and O atoms, which belong to either the N2 O2 moiety of additional Zn-Salphen complex molecules or N and/or O atoms that are present in other guest type molecules, has propelled the versatility of these kind of complexes. The latter has delivered access to their wide use as building blocks in self-assembled nanoarchitectures [11], auto-organized nanofibers [12], and many other different supramolecular host-guest systems [13,14,15]. This situation has inspired new strategies to develop a variety of supramolecular applications, such as self-assembled soft-matter [16,17,18,19], supramolecular sensors [20,21,22,23], and supramolecular catalysis [24,25,26]
As a proof of concept, we demonstrate synthesis of functional polymers via radical co-polymerization with a suitable fixed ratio of acrylic that the complex can be used in different ratios as an anion recognition building block during the monomers n-butyl acrylate (nBuA) and methyl metacrylate (MMA)
Summary
Zn-Salphen complexes are compounds that can be synthesized by the condensation of o-phenylene diamine and salicylaldehyde derivatives, which, after coordination with Zn(II), form a wide range of imine-based complexes showing interesting and useful chemical features. Their advantageous easy tuning properties through chemical functionalization of the aryl groups from the ligand part has facilitated their use in a wide range of applications: e.g., chemosensors for anions [1,2], organic photo-emitters in optoelectronics [3,4,5,6], and as catalysts [7,8,9] With respect to their molecular geometry, Zn-Salphen complexes counterintuitively present a planar square N2 O2 cavity after being coordinated to the (Lewis-acidic) Zn(II) center, where the geometry imposed by the Salphen ligand leaves a non-hindered vacant site for further supramolecular interactions with suitable Lewis-basic guests (e.g., via coordination, coulombic, etc.) [10]. This situation has inspired new strategies to develop a variety of supramolecular applications, such as self-assembled soft-matter [16,17,18,19], supramolecular sensors [20,21,22,23], and supramolecular catalysis [24,25,26]
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