Heteroditopic Receptors for Ion‐Pair Recognition

McConnell, Anna J.; Beer, Paul D.

doi:10.1002/anie.201107244

Cited by 243 publications

(171 citation statements)

References 56 publications

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“…16 Heteroditopic receptors for cation−anion pair recognition have also been developed in molecular systems bearing a crown-ether-fused phenylurea, where co-operative ion-binding properties were successfully achieved. 17,18 A variety of detection techniques based on properties such as electrical conductivity, magnetic properties, and optical responses have been utilized for cation and anion sensing. Among these techniques, the use of optical detection in terms of absorption and emission spectra is a simple and conventional technique for achieving high-resolution sensing.…”

Section: Introductionmentioning

confidence: 99%

Cation–Anion Dual Sensing of a Fluorescent Quinoxalinone Derivative Using Lactam–Lactim Tautomerism

et al. 2015

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A quinoxalinone derivative capable of lactam-lactim tautomerization was designed as a new fluorescence probe for sensing of cation (M(+) = Li(+) and Na(+)) and anion (X(-) = F(-), Cl(-), Br(-), and CH3COO(-)) in organic solvents. In THF, the minor lactam tautomer exhibited a weak fluorescence band at 425 nm with a typical Stokes shift of ∼4400 cm(-1), whereas the major lactim tautomer exhibited an intense fluorescence band at 520 nm with large Stokes shift of ∼8900 cm(-1) due to excited-state intramolecular proton transfer (ESIPT). The presence of either cations or anions was found to promote lactim-to-lactam conversion, resulting in the lowering of the ESIPT fluorescence. The lone pairs on the alkylamide oxygen and the quinoxalinone ring nitrogen of the lactam were found to bind Li(+) to form a 1:2 coordination complex, which was confirmed by single crystal X-ray structural analysis and fluorescent titrations. In addition, the N-H bond of the lactam was able to recognize anions via N-H···X hydrogen bonding interactions. Where X = F(-) or CH3COO(-), further addition of these anions caused deprotonation of the lactam to generate an anionic state, consistent with the crystal structure of the anion prepared by mixing tetrabutylammonium fluoride and the quinoxalinone derivative in THF. Dual cation-anion-sensing responses were found to depend on the ion-recognition procedure. The anionic quinoxalinone derivative and its Li(+) complex, which are formed by the addition of CH3COO(-) and Li(+), respectively, displayed different fluorescence enhancement behavior due to the two anions exchanging with each other.

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Section: Introductionmentioning

confidence: 99%

Cation–Anion Dual Sensing of a Fluorescent Quinoxalinone Derivative Using Lactam–Lactim Tautomerism

et al. 2015

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“…Most of the calixarene–guest pairs employed so far have been either neutral or oppositely charged . When the guest moiety is charged and the host is neutral, ion‐pairing effects may significantly hamper the complexation efficiency and, as a consequence, polymer growth. Several strategies have been devised to overcome such a growth‐limiting effect.…”

Section: Introductionmentioning

confidence: 99%

Ring/Chain Morphology Control in Overall‐Neutral, Internally Ion‐Paired Supramolecular Polymers

Manganaro

Pisagatti

Notti

et al. 2017

Chemistry A European J

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The self-assembly of internally ion-paired, neutral AA/BB-type supramolecular polymers composed of complementary di-ionizable homoditopic pairs of monomers is reported. Host-to-guest double-proton transfer mediates the recognition between bis-calix[5]arenedicarboxylic acids and α,ω-diaminoalkanes to yield cyclic, doughnut-shaped assemblies with morphologies (i.e., cyclic vs. linear) that can be controlled by means of external chemical stimuli. The behavior of these intriguing aggregates, both in solution and on surfaces, has been investigated by a combination of H and DOSY NMR spectroscopy, light-scattering, and atomic force microscopy.

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“…15–17 These receptors have been applied in a number of areas of research such as membrane transport, extraction, salt solubilization and sensing applications. 18–20 …”

Section: Introductionmentioning

confidence: 99%

Lithium-selective phosphine oxide-based ditopic receptors show enhanced halide binding upon alkali metal ion coordination

et al. 2013

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Previous work on a ditopic receptor based on a tripodal phosphine oxide core demonstrated preferential enhancement of bromide binding over chloride or iodide in the presence of lithium cation. Current studies on an elongated receptor provide evidence that preferential bromide binding enhancement in the presence of lithium cation is common to this receptor class in general, and that lengthening of the receptor results in an overall increase in halide association. Furthermore, the extended receptor shows a strong preference for Li+ binding in solution.

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Heteroditopic Receptors for Ion‐Pair Recognition

Cited by 243 publications

References 56 publications

Cation–Anion Dual Sensing of a Fluorescent Quinoxalinone Derivative Using Lactam–Lactim Tautomerism

Cation–Anion Dual Sensing of a Fluorescent Quinoxalinone Derivative Using Lactam–Lactim Tautomerism

Ring/Chain Morphology Control in Overall‐Neutral, Internally Ion‐Paired Supramolecular Polymers

Lithium-selective phosphine oxide-based ditopic receptors show enhanced halide binding upon alkali metal ion coordination

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