Artificial Receptors for the Recognition of Phosphorylated Molecules Amanda E. Hargrove, Sonia Nieto, Tianzhi Zhang, Jonathan L. Sessler,* and Eric V. Anslyn* Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, United States Universidad de Zaragoza, Zaragoza, Spain Henkel Corporation, Rocky Hill, Connecticut 06067 Department of Chemistry, Yonsei University, Seoul, 120-749 Korea

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Artificial receptors for the recognition of phosphorylated molecules

Anion coordination and anion-templated assembly: Highlights from 2002 to 2004

The development of compartmental macrocyclic Schiff bases and related polyamine derivatives

This critical review is dedicated to the anion complexation chemistry of amide- and urea-functionalized (benzo)pyrroles, such as pyrroles, indoles, carbazoles, isoindoles, naphthalenodipyrroles and benzodipyrroles. It provides a comprehensive overview of these simple and neutral anion sensors from the first examples up to very recent studies. There is a discussion of a gradual progress made over time, often based on careful analysis of the properties of former generations that have subsequently led to obtaining excellent effectivities and selectivities. The influence of these species on other fields of chemistry and their applications there are also discussed (57 references).

Amide- and urea-functionalized pyrroles and benzopyrroles as synthetic, neutral anion receptors

Amidopyrroles: from anion receptors to membrane transport agents.

Dicopper(II) and dinickel(II) complexes of Schiff-base macrocycles derived from 5,5-dimethyl-1,9-diformyldipyrromethane

Four examples of bis-amidopyrrole derivatives of pyrrole-2,5-diacetic acid have been prepared. The reaction of diethyl pyrrole-2,5-diacetate with a large excess (24 equiv.) of N,N-dimethylethylenediamine gave N,N′-bis(2-dimethylaminoethyl)-1H-pyrrole-2,5-diacetamide (1). Three further examples, N,N′-bis[2-(2-pyridyl)ethyl]-1H-pyrrole-2,5-diacetamide (2), N,N′-bis(2-pyridylmethyl)-1H-pyrrole-2,5-diacetamide (3) and N,N′-dibenzyl-1H-pyrrole-2,5-diacetamide (4), were prepared in a one pot procedure by converting pyrrole-2,5-diacetic acid into the N-hydroxysuccinimide ester and then reacting this with four equivalents of the appropriate amine, 2-(2-aminoethyl)pyridine, 2-aminomethylpyridine or benzylamine, respectively. Compounds 1–4 are shown to be effective anion receptors in acetonitrile-d3 solution, with comparable binding affinities to those found for simple pyrrole-2,5-dicarboxamides, despite possessing a more flexible hydrogen bonding array.

Synthesis and anion binding behaviour of diamide derivatives of pyrrole-2,5-diacetic acid

Three copper(II) complexes of (L1)–, [CuL1Cl] (1), [CuL1Br]n (2) and [Cu2(L1)2(μ1,3-NCS)2] (3), and two copper(II) complexes of HL1, [Cu(HL1)X2] (X = Cl–, 4; X = Br–, 5), have been prepared and characterised [where HL1 is the Schiff-base ligand derived from pyrrole-2-carbaldehyde and 2-aminomethylpyridine]. The removal of a chloride ion and deprotonation of [Cu(HL1)Cl2] (4) to form [CuL1Cl] (1) worked well. However, attempts to protonate [CuL1Cl] with HCl to re-form [Cu(HL1)Cl2] were not successful. X-ray structure determinations revealed that 1 is a N3Cl-coordinated square-planar copper(II) monomer [CuL1Cl], whereas 3 is a doubly end-to-end thiocyanate-bridged square-pyramidal copper(II) dimer [Cu2(L1)2(μ1,3-NCS)2]. The structure determinations on 4 and 5 showed that in both cases the copper(II) ion is in a distorted square-planar N2X2 environment, with the pyrrole NH remaining non-deprotonated and uncoordinated. Variable-temperature magnetic susceptibility investigations carried out on the end-to-end thiocyanate doubly bridged square-pyramidal copper(II) dimer 3 showed that no magnetic coupling occurs between the two copper(II) ions; it exhibits Curie-like magnetic behaviour.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Monomeric and Dimeric Copper(II) Complexes of a Pyrrole-Containing Tridentate Schiff-Base Ligand

The preparation of diethyl 2,2′-(2,5-pyrrolidinediylidene)bisacetate (2) from diethyl 3,6-dioxooctanedioate (1) is detailed, as is the subsequent conversion of 2 into its tautomer, diethyl pyrrole-2,5-diacetate (3), by acid catalysis. Alternatively, base hydrolysis of 2 gives pyrrole-2,5-diacetic acid (4) in good yield as long as the reaction solution is subsequently acidified to pH = 1 before extraction. In D2O solution, in the absence of added base, the pyrrole ring C–H protons are rapidly exchanged for deuterons. The X-ray structures of 2 and 4 are reported and confirm the earlier prediction, made primarily on the basis of the 1H NMR data, that 2 is a pyrrolidine tautomer while 4 is a pyrrole tautomer. Hydrogen bonding, intramolecular in the case of 2 and intermolecular in the case of 4, is a feature of both structurally characterised compounds.

Syntheses, structures and tautomers of 2,5-disubstituted pyrroles

Copper(II) and palladium(II) complexes of a terdentate pyrrolidine diester ligand

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