Anion Recognition in Supramolecular Chemistry by Brett M. Rambo, Eric S. Silver (auth.), Philip A. Gale, Wim

By Brett M. Rambo, Eric S. Silver (auth.), Philip A. Gale, Wim Dehaen (eds.)

Brett M. Rambo ∙ Eric S. Silver ∙ Christopher W. Bielawski ∙ Jonathan L. Sessler Covalent Polymers Containing Discrete Heterocyclic Anion Receptors Philip A. Gale ∙ Chang-Hee Lee Calix[n]pyrroles as Anion and Ion-Pair Complexants Wim Dehaen Calix[n]phyrins: Synthesis and Anion attractiveness Hiromitsu Maeda Acyclic Oligopyrrolic Anion Receptors Jeffery T. Davis Anion Binding and shipping by way of Prodigiosin and Its Analogs Hemraj Juwarker ∙ Jae-min Suk ∙ Kyu-Sung Jeong Indoles and similar Heterocycles Pavel Anzenbacher Jr. Pyrrole-Based Anion Sensors, half I: Colorimetric Sensors Pavel Anzenbacher Jr. Pyrrole-Based Anion Sensors, half II: Fluorescence, Luminescence, and Electrochemical Sensors Ermitas Alcalde ∙ Immaculada Dinarès ∙ Neus Mesquida Imidazolium-Based Receptors Nathan L. Kilah ∙ Paul D. Beer Pyridine and Pyridinium-Based Anion Receptors Kevin P. McDonald ∙ Yuran Hua ∙ Amar H. Flood 1,2,3-Triazoles and the increasing application of cost impartial CHlllAnion Interactions

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A. -H. A. -H. Lee Abbreviation NMR Nuclear magnetic resonance 1 Introduction Calix[4]pyrroles (meso-octaalkylporphyrinogens) are a class of tetrapyrrolic macrocycle first synthesized in the late nineteenth century by Baeyer via the acid (HCl)-catalysed condensation of pyrrole and acetone [1]. Contemporaneously with Bayer, Dennstedt and Zimmermann studied this reaction using ‘Chlorzink’ as the acid catalyst [2–4].

3 The X-ray crystal structures of the CsCl (left) and 1-butyl-3-methylimidazolium chloride (right) complexes of compound 1. Certain hydrogen atoms and solvent molecules have been omitted for clarity Calix[n]pyrroles as Anion and Ion-Pair Complexants 47 assumption that calix[4]pyrrole acts as a simple anion receptor (1) was re-examined and the authors considered solvation and ion-pairing effects (2). CP þ ClÀ ! ½CP À ClŠÀ (1) ½CPŠsolv þ ½ClÀ Rþ Šsolv !

However, the observed affinities are in agreement with the so-called Hofmeister bias, as chloride is a more hydrophobic anion (DGh ¼ À340 KJ molÀ1) than fluoride anion (DGh ¼ À465 KJ molÀ1) [21, 66]; chloride anion was thus expected to be extracted more readily than this latter, more hydrophilic species. Support for this rationalization came from the finding that octamethylcalix[4]pyrrole and PMMA were both capable of extracting TBACl, but 35% less efficiently than polymer 50. In the case of TBAF only polymer 50 was capable of removing fluoride from the aqueous layer.

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