Weak interactions between resorcinarenes and diquaternary alkyl ammonium cations

Mansikkamäki, Heidi; Schalley, Christoph A.; Nissinen, Maija; Rissanen, Kari

doi:10.1039/b415401k

Cited by 71 publications

(51 citation statements)

References 57 publications

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“…The high affinity of the hosts towards the di-tertiary ammonium salt 5c could be explained by the high charge concentration and a suitable size of the guest 5c. The second binding constant K 2 was much lower in all cases with 5c, highlighting the well known 14,16,20 interference of the bulk methanol. Titration study was not possible for the dication 4c due to its extremely low solubility in methanol.…”

Section: Solution Studiesmentioning

confidence: 84%

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Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

2015

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The binding of different categories of alkyl ammonium (secondary and tertiary mono-and diammonium) salts by resorcinarenes and a pyrogallarene through weak interactions were analysed in all phases. 1 H NMR spectroscopy and electrospray ionisation mass spectrometry were utilized in analysing the complexes in solution and in the gas phase respectively. The 1 H NMR titration studies in methanol-d 4 reveal the association constants for the 1:1 complexes to vary according to the electronic properties of hosts as well as the size, geometric orientation and charge concentration of the guest cations with binding constants of up to 950 M -1 in some cases. Mass spectrometry reveals 1:1 monomeric and 1:2 dimeric complexes in the gas phase. Six co-crystals, three of which are dimeric host-guest capsular assemblies, two open inclusion complexes and a pseudocapsular methanol solvate were analysed in the solid state through single-crystal X-ray diffraction. The crystal structures confirm the complexes to be held together by multiple cation···π, CH···π and hydrogen bond interactions.

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Section: Solution Studiesmentioning

confidence: 84%

“…14,17,19,25,26 The alkyl 2 -DABCO dication has templated several structures with resorcinarenes such as 1:1 inclusion complexes, 14 dimeric capsular assemblies and nanotubes. 25 Dimethylpiperazine has been shown to deprotonate resorcinarenes and templates a directly hydrogen bonded assembly.…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

2015

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“…The anions were added as their tetrabutylammonium (TBA) salts, since the larger cation was thought to be less susceptible to interact with the host molecule compared to the smaller tetramethylammonium counter cation. [8] With Cl -, Br -, I -, NO 3 -, PF 6 -and BF 4 -anions the addition of ten equivalents of the anion caused no changes in the 1 H NMR spectra of 4, which suggested that very weak or no binding was taking place with these anions in solution. However, upon the addition of F -anions significant changes were observed in the 1 H NMR spectrum of 4 as both the -NH and -NH 2 amine resonances shifted downfield, which was attributed to anion binding taking place ( Figure 4).…”

Section: Solution Binding Studiesmentioning

confidence: 95%

Resorcinarene Podand with Amine‐Functionalized Side Arms – Synthesis, Structure, and Binding Properties of a Neutral Anion Receptor

et al. 2009

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The synthesis and structure of a neutral resorcinarene host bearing four amine‐functionalized side arms is described. The anion binding properties were investigated in solution by 1H NMR spectroscopic titration and diffusion experiments and in the gas phase by mass spectrometric studies. It was observed that in solution 1:2 (host/guest) complexes were formed between the resorcinarene host and the basic fluoride and acetate anions, whereas in the gas phase 1:1 complexes with other anions (Cl–, HCOO–, NO3–, and BF4–) were detected additionally. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…Mass spectrometric evidence for these bromide-containing assemblies has been reported by Schalley and coworkers. 57 In contrast to the anions, the nature of the cation has only a minor influence on the type of voltammetric behavior observed for cobaltocenium in the presence of resorcinarene hosts. An interesting finding in our experiments is that the resorcinarene capsules show a strong preference to encapsulate cobaltocenium versus tetra-alkylammonium cations, as these did not interfere when present in large excess, as required for the cation of the supporting electrolyte.…”

Section: Electrochemistry Of Inclusion Complexes Formed By Cavitand-tmentioning

confidence: 99%

Molecular Encapsulation of Redox‐Active Guests

Kaifer

2009

Electrochemistry of Functional Supramolecular Systems

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Weak interactions between resorcinarenes and diquaternary alkyl ammonium cations

Cited by 71 publications

References 57 publications

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

Resorcinarene Podand with Amine‐Functionalized Side Arms – Synthesis, Structure, and Binding Properties of a Neutral Anion Receptor

Molecular Encapsulation of Redox‐Active Guests

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