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 acceptance 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 comparable 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 software of cost impartial CHlllAnion Interactions

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64 6 Catalysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 68 7 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 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].

A. -H. Lee Calix[4]pyrroles functionalized at a pyrrole CH position [34] are attractive synthetic goals as the substituents can modulate the affinity of the calixpyrrole for anionic guests [35], act as a reporter group [36] or provide a point of attachment for immobilization of the macrocycle [37]. One of the first examples studied in terms of the effect of the substitutents on anion-binding affinity was octabromomeso-octamethylcalix[4]pyrrole 10 [38]. This compound was shown to have an enhanced affinity for anions in CD2Cl2 as compared to parent macrocycle 1.

4 Â 103 MÀ1. A. -H. Lee Calix[4]pyrroles functionalized at a pyrrole CH position [34] are attractive synthetic goals as the substituents can modulate the affinity of the calixpyrrole for anionic guests [35], act as a reporter group [36] or provide a point of attachment for immobilization of the macrocycle [37]. One of the first examples studied in terms of the effect of the substitutents on anion-binding affinity was octabromomeso-octamethylcalix[4]pyrrole 10 [38]. This compound was shown to have an enhanced affinity for anions in CD2Cl2 as compared to parent macrocycle 1.

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