Bis-cation salt complexation by meso-octamethylcalix[4]pyrrole: linking complexes in solution and in the solid state

Caltagirone, Claudia; Bill, Nathan L.; Gross, Dustin E.; Light, Mark E.; Sessler, Jonathan L.

doi:10.1039/b916113a

Cited by 23 publications

(14 citation statements)

References 28 publications

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“…In recent times, the design and study of ditopic receptors capable of simultaneous complexation of anion and cation have attracted intense interest but they are omitted in this review. 87 Spectacular advances in the selective encapsulation of anions have been achieved using oligocyclic polyamides. In 1997 Anslyn et al designed an amide-linked C 3 -symmetric cyclophane 21 capable of including anions exclusively through hydrogen bonding (Fig.…”

Section: Macrooligocyclic Polyamidesmentioning

confidence: 99%

Anion binding in covalent and self-assembled molecular capsules

2010

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This critical review describes selected examples extracted from the extensive literature generated during the past 42 years on the topic of anion binding in molecular capsules. The goal of including anions in molecular capsules emerges from the idea of incorporating the traits exhibited by biological receptors into synthetic ones. At the outset of this research area the capsules were unimolecular. The scaffold of the receptor was designed to covalently link a series of functional groups that could converge into a cavity and to avoid its collapse. The initial examples involved the encapsulation of one monoatomic spherical anion. With time, the cavity size of the receptor was increased and encapsulation of polyatomic anions and co-encapsulation became a reality. Synthetic economy fueled the use of aggregates of self-complementary molecules rather than one large molecule as capsules. The main purpose of this review is to give a general overview of the topic which might be of interest to supramolecular or non supramolecular chemists alike (149 references).

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Section: Macrooligocyclic Polyamidesmentioning

confidence: 99%

Anion binding in covalent and self-assembled molecular capsules

2010

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“…When a calix[4]pyrrole is bound to an anion it adopts a cone conformation while forming a “cup‐like” π electron cloud by means of oriented pyrrole rings . Upfield chemical shifts belonging to methyl and methylene protons of CTA clearly indicate that calix[4]pyrrole core of 2b acts as an ion pair receptor for both tethered carboxylate unit and CTA, binding the ammonium cation of CTA via cation–π interactions and the tethered carboxylate via hydrogen bonding , . This was also supported by the existence of correlated 2D‐NOESY signals between the methyl protons of CTA and pyrrole CH protons of calix[4]pyrrole core (Figure S22).…”

Section: Resultsmentioning

confidence: 86%

Counter Cation Dependent and Stimuli Responsive Supramolecular Polymers Constructed by Calix[4]pyrrole Based Host–Guest Interactions

Yuvayapan

Aydogan

2018

Eur J Org Chem

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Carboxylate tethered calix[4]pyrroles in the form of their tetrabutylammonium (TBA) and cetyltrimethylammonium (CTA) salts were synthesized via an acid base reaction between the corresponding carboxylic acid functionalized calix[4]pyrrole and tetrabutyl‐ or cetyltrimethylammonium hydroxide. The host–guest recognition motif based on these calix[4]pyrrole macrocycles and tethered carboxylate units was employed to construct novel A–B type supramolecular polymers from low molecular weight monomers in chloroform. These supramolecular polymers were found to be dependent on the counter cation in terms of the properties of supramolecular polymers. 1H‐, DOSY‐, NOESY‐NMR spectroscopic analyses, viscosity measurements, and SEM results were used to characterize supramolecular polymers and revealed that the CTA cation becomes a direct part of supramolecular polymer via cation–π interactions between the ammonium part of CTA and carboxylate‐bound calix[4]pyrrole, effecting the overall properties of supramolecular polymers such as viscosity, gel formation, and drawing fibers. Additionally, reversible pH‐ and thermo‐responsiveness of the supramolecular polymers were demonstrated for the first time for an anion recognition induced calix[4]pyrrole based supramolecular polymer.

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“…This cation recognition chemistry is not limited to simple imidazolium salts. In fact, bis(imidazolium) cations have been used to tether together two separate anion‐bound calixpyrrole complexes to produce sandwich‐type structures in solution and in the solid state 21. It was thus thought that the bis(imidazolium) cation 5 (a dibromide anion salt) could promote the self‐assembly of nanoparticles such as Au⋅[ 1 ] n and Au⋅[ 2 ] n .…”

Section: Resultsmentioning

confidence: 99%

Reversible Assembly and Disassembly of Receptor‐Decorated Gold Nanoparticles Controlled by Ion Recognition

Aydogan

Lee

et al. 2014

Chemistry A European J

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The controlled assembly of randomly dispersed colloidal particles can provide access to materials with advanced optical and electronic properties while providing fundamental insights into self-assembly processes in nature and nanotechnology. Typically, self-assembled nanoparticles are prepared by exploiting electrostatic interactions, lithographic techniques, and covalently linked molecular scaffolds. This results in static morphologies that cannot be disassembled easily. On the other hand, having access to systems that can be assembled or disassembled in a controlled manner could allow for in-depth understanding of the nanoparticles as well as rational control over the morphology and fundamental properties of the resulting constructs. If the changes in aggregation are induced by a specific external chemical stimulus, it could also permit the development of new chemosensors. Here we demonstrate the reversible assembly and disassembly of gold nanoparticles achieved by modulating the noncovalent interactions between surface-bound calix[4]pyrroles and added bis-imidazolium cations. We also demonstrate the use of these nanoparticles in the selective sensing of anions.

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Bis-cation salt complexation by meso-octamethylcalix[4]pyrrole: linking complexes in solution and in the solid state

Cited by 23 publications

References 28 publications

Anion binding in covalent and self-assembled molecular capsules

Anion binding in covalent and self-assembled molecular capsules

Counter Cation Dependent and Stimuli Responsive Supramolecular Polymers Constructed by Calix[4]pyrrole Based Host–Guest Interactions

Reversible Assembly and Disassembly of Receptor‐Decorated Gold Nanoparticles Controlled by Ion Recognition

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