Octamethyl-octaundecylcyclo[8]pyrrole:  A Promising Sulfate Anion Extractant [J. Am. Chem. Soc. 2007, 129, 11020−11021].

Eller, Leah R.; Stępień, Marcin; Fowler, Christopher J.; Lee, Jeong Tae; Sessler, and Jonathan L.; Moyer, Bruce A.

doi:10.1021/ja077858+

Cited by 21 publications

(30 citation statements)

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“…[3] Materials that could allow for such separations are thus of potential interest in a wide range of applications. [4] Polymeric systems are particularly attractive in this regard because they are generally easy to isolate from solutions or mixtures.…”

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confidence: 99%

“…Recently, we reported that copolymers of a polymerizable derivative 2 (Scheme 1) of octamethylcalix [4]pyrrole (1) [5] and methyl methacrylate (MMA) are effective at extracting tetrabutylammonium chloride or fluoride from aqueous media. [6] Unfortunately, these polymeric materials displayed relatively low affinities for the corresponding salts containing cations less soluble in organic media (e.g., Na and K).…”

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confidence: 99%

“…Herein, we report the synthesis, characterization, and extraction properties of mixed MMA copolymers containing pendant calix [4]pyrrole subunits known to bind halide anions in a 1:1 ratio in organic media [5] and benzo- [15]crown-5 subunits capable of forming 2:1 sandwich complexes with potassium cations. [7] It was thus expected that strong, potentially mutually enhancing, interactions would enable these polymeric materials to extract potassium halide salts, such as KCl and KF, from aqueous solutions.…”

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confidence: 99%

“…Copolymers 4-6 (Scheme 1) were prepared from MMA, calix [4]pyrrole 2, and the benzo- [15]crown-5 derivative 7 [9] using conventional free-radical polymerization techniques. [10] In general, azoisobutyronitrile (1 mol %) was added to THF solutions of these monomers in various ratios.…”

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confidence: 99%

“…Initial qualitative evidence that copolymer 4, which contains both calix [4]pyrrole and crown ether subunits, could extract chloride salts into organic media came from a visual test involving 9, a water-soluble dye that contains a chloride counteranion. Treatment of an aqueous solution of 9 (25.5 mm) with a CH 2 Cl 2 solution of copolymer 4 (effective concentration of the calix [4]pyrrole and crown ether repeat units was 1.56 and 1.22 mm, respectively) resulted in a colored organic phase ( Figure 1).…”

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Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

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Fishing for KF: Potassium fluoride and chloride salts can be extracted from aqueous media using poly(methyl methacrylate)s containing pendant calix[4]pyrrole and crown ether groups (see picture). These polymers are able to extract these salts much more efficiently than calixpyrrole, crown ether, linked crown ether calixpyrrole monomers, polymers containing either recognition unit, or poly(methyl methacrylate) controls.

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Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

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Porphyrins and Expanded Porphyrins as Receptors

Sessler

Karnas

Sedenberg

2012

Supramolecular Chemistry

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This chapter summarizes recent efforts to use porphyrins and expanded porphyrins as receptors. These unique macrocycles bear resemblance to naturally occurring tetrapyrrolic pigments and have been studied extensively as building blocks for a variety of functional molecular receptors. The introduction discusses the inherent characteristics of porphyrins and their analogs from the perspective of receptor design and is designed to highlight key features. These features include ease of synthesis and functionalization, the hydrogen‐bonding ability of the constituent pyrrolic NH protons, and the fact that the systems in question are often highly colored. This latter feature has afforded an extremely useful means of analyzing host–guest interactions. Because of space limitations, not all of the literature on this topic could be covered in a comprehensive manner. The definition of “receptor” is also limited to species that are thought to be operated via strictly noncovalent‐ or supramolecular‐type interactions. However, this definition is expanded in a few special cases. The goal of this article is not to cite every published article on this topic, but to highlight interesting examples of porphyrin and expanded porphyrins and their utility as receptors. An effort has also been made to describe the analytical techniques used to characterize the resulting host–guest ensembles. This chapter is organized according to the type of guest. One section covers the relatively new area of supramolecular π–π interactions involving porphyrins and nanomaterials, such as fullerenes and nanotubes. Another section discusses porphyrins as receptors for biological entities, including saccharides, peptides, and proteins, as well as DNA. The next section covers porphyrins and expanded porphyrins as anion receptors. This latter treatment includes a discussion of supramolecular electron‐transfer dyads. The use of porphyrins in sensing applications is also presented in summary form. Finally, a perspective on this rapidly growing field of supramolecular chemistry is included in the final remarks. It is hoped that the combination of cited references and listed further readings will allow the interested reader to learn more about this fast‐evolving and fascinating topic.

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Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

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Fischen nach KF: Kaliumfluoride und ‐chloride können aus wässrigen Medien mit Poly(methylmethacrylaten) extrahiert werden, die Calix[4]pyrrol‐ und Kronenetherfunktionen tragen (siehe Bild). Mit diesen Polymeren gelingt die Extraktion viel effizienter als mit Kontrollsubstanzen wie Calixpyrrolen, Kronenethern, verbrückten Kronenether‐Calixpyrrol‐Monomeren, Polymeren mit einer der beiden Erkennungseinheiten oder Poly(methylmethacrylat).

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Octamethyl-octaundecylcyclo[8]pyrrole: A Promising Sulfate Anion Extractant [J. Am. Chem. Soc. 2007, 129, 11020−11021].

Cited by 21 publications

References 0 publications

Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

Porphyrins and Expanded Porphyrins as Receptors

Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

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