First Cryptand-Like Calixpyrrole:  Synthesis, X-ray Structure, and Anion Binding Properties of a Bicyclic[3,3,3]nonapyrrole

Bucher, Christophe; Zimmerman, Rebecca S.; Lynch, Vincent M.; Sessler, Jonathan L.

doi:10.1021/ja016629z

Cited by 98 publications

(57 citation statements)

References 10 publications

(9 reference statements)

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“…The mono(TTF)-calix [4]pyrrole 51 was synthesized as outlined in Scheme 12. The tripyrranedicarbaldehyde 49 can be prepared [52] by condensation of pyrrole and acetone, followed by a Clezy formylation. Reduction of the formyl groups in 49 with sodium borohydride/lithium bromide in anhydrous THF/MeOH produced the bis(hydroxymethyl)tripyrrane 50 in 76% yield.…”

Section: A Mono(pyrrolo)-ttf Calix[4]pyrrole As An Anion Sensormentioning

confidence: 99%

Pyrrolo‐Tetrathiafulvalenes and Their Applications in Molecular and Supramolecular Chemistry

2003

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Although tetrathiafulvalene and its derivatives have been extensively studied as π-electron donors in the fields of molecular organic metals and electrically conducting materials for more than 30 years, the intriguing potential of tetrathiafulvalene as a building block in molecular and supramolecular chemistry has only recently been developed. Progress in synthetic tetrathiafulvalene chemistry has enabled the preparation of elaborate molecular architectures and, in recent

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Section: A Mono(pyrrolo)-ttf Calix[4]pyrrole As An Anion Sensormentioning

confidence: 99%

Pyrrolo‐Tetrathiafulvalenes and Their Applications in Molecular and Supramolecular Chemistry

2003

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“…To this end, the basic CP scaffold has been modified, either by extending the size (calix[n]pyrrole), [30][31][32][33][34] or by generating double-cavity or cryptand-like derivatives. [35,36] Related work has involved the study of hybrid receptors obtained by substituting one or more of the pyrrole subunits in CP by other heterocyclic rings, such as pyridine, thiophene, and furan. [15,[37][38][39][40][41][42][43][44] Attachment of substituents to CP has also been used to modify the binding properties, and has led to systems capable of binding selectively certain ions or neutral molecules.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Dynamics of Calix[4]pyrrole: Effect of Solvent and Fluorine Substitution

Blas

López-Bes

Márquez

et al. 2007

Chemistry A European J

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Molecular dynamics simulations show that calix[4]pyrrole (CP) and octafluorocalix[4]pyrrole (8F-CP) are extremely flexible molecules. CP mainly adopts the 1,3-alternate conformation in all the solvents, although the percentage of alternative conformations increases in polar solvents, especially those with good hydrogen-bonding acceptor properties. However, in the case of 8F-CP, the cone conformation is the most populated in some solvents. Transitions between conformers are common and fast, and both CP and 8F-CP can adopt the cone conformation needed for optimum interaction with anions more easily than would be predicted on the basis of previous gas-phase calculations. Furthermore, the present studies show that when a fluoride anion is specifically placed initially in close proximity to CP and 8F-CP in their respective 1,3-alternate conformations, an extremely fast change to the cone conformation is observed in both cases. The results suggest that preorganization does not represent a major impediment to anion-binding for either CP or 8F-CP, and that ion-induced conformational changes can follow different mechanisms depending on the solvent and the chemical substituents present on the calix[4]pyrrole beta-pyrrolic positions.

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“…In this case, the neutral substrate, ethylenediamine, was found within the cavity, with the corresponding solution phase binding affinity being 1,500 M À1 in CDCl 3 . Slightly thereafter, the Sessler group reported the synthesis and structure of a '3-D calixpyrrole' 63 and its oxidized analogue 64 [77,78]. Neither of these systems contains a cavity-like void space.…”

Section: -46mentioning

confidence: 99%

Calix[n]pyrroles as Anion and Ion-Pair Complexants

Gale

Lee

2010

Topics in Heterocyclic Chemistry

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This chapter covers advances in calixpyrrole chemistry and specifically in the application of these species as anion and ion-pair complexation agents over the last 5 years. Over this time, the chemistry of these easy-to-make macrocycles advanced with the discovery of the ion-pair complexation properties of calixpyrroles, in addition to the development of strapped calixpyrroles that incorporate extra hydrogen bond donors and possess higher affinities for anions than the parent macrocycle. Calixpyrroles have also been employed as anion complexants in solvent-solvent extraction and in polymers. They have also been shown to function as lipid bilayer transport agents for salts and as organocatalysts.

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First Cryptand-Like Calixpyrrole: Synthesis, X-ray Structure, and Anion Binding Properties of a Bicyclic[3,3,3]nonapyrrole

Cited by 98 publications

References 10 publications

Pyrrolo‐Tetrathiafulvalenes and Their Applications in Molecular and Supramolecular Chemistry

Pyrrolo‐Tetrathiafulvalenes and Their Applications in Molecular and Supramolecular Chemistry

Exploring the Dynamics of Calix[4]pyrrole: Effect of Solvent and Fluorine Substitution

Calix[n]pyrroles as Anion and Ion-Pair Complexants

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