Selective Nitrate Binding in Competitive Hydrogen Bonding Solvents: Do Anion–π Interactions Facilitate Nitrate Selectivity?

Watt, Michelle; Zakharov, Lev N.; Haley, Michael M.; Johnson, Darren W.

doi:10.1002/anie.201303881

Cited by 75 publications

(62 citation statements)

References 41 publications

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“…However, crystal and solution studies have also demonstrated the existence of alternative W and S conformations in this general class of bisurea arylethynyl receptors. 29–31 …”

Section: Resultsmentioning

confidence: 99%

“Off-on” aggregation-based fluorescent sensor for the detection of chloride in water

et al. 2015

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Receptors selective for anions in aqueous media are a crucial component in the detection of anions for biological and environmental applications. Recent sensor designs have taken advantage of systems known to aggregate in solution, eliciting a fluorescent response. Herein, we demonstrate a chloride-selective fluorescent response of receptor 1+, based on our well-established class of 2,6-bis(2-anilinoethynyl)pyridine bisureas. The fluorescence intensity ratio of 1+·Cl− aggregates in water is four times larger than the next most fluorescent anion complex, 1+·ClO4−. In addition, 1H NMR spectroscopic titrations demonstrate 1+ binds chloride more strongly than other biologically relevant anions in solutions of both DMSO-d6 and 50/50 DMSO-d6/MeCN-d3.

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“…However, crystal and solution studies have also demonstrated the existence of alternative W and S conformations in this general class of bisurea arylethynyl receptors. 29–31 …”

Section: Resultsmentioning

confidence: 99%

“Off-on” aggregation-based fluorescent sensor for the detection of chloride in water

et al. 2015

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“…[78] The desired selectivity of 29 for NO 3 − over halides was supported by 1 H NMR titrations in 10% DMSO/CDCl 3 . The X-ray crystal structure favors an uncommon explanation for selectivity, namely an anion–π type interaction between NO 3 − and the alkyne attached to the central arene, where the anion rests offset from the center of a tripodal binding pocket (Figure 17 colored inset).…”

Section: Charged Speciesmentioning

confidence: 99%

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Vonnegut

Tresca

Johnson

et al. 2015

Chemistry An Asian Journal

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The aryl–ethynyl linkage has been extensively employed in the construction of hosts for a variety of guests. Uses range from ion detection (e.g., of metal cations in the environment or industrial waste and of anions prevalent in nature), to molecular mimics for biological systems, and to applications targeting future safety issues (such as CO2 capture and indicators for the manufacture of chemical weapons). This Focus Review examines the utilization of the aryl–ethynyl linkage in engineering host molecules for a variety of different guests, and how the alkyne unit plays an integral part as both a rigid scaffolding section in host geometry design as well as a linker to allow conjugative communication between discrete π-electron systems.

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“…We have previously reported on a family of modular arylethynyl receptors for anion binding and fluorescent sensing using 2,6-bis(2-anilinoethynyl)pyridine (18-25), -bipyridine (24, 26-28), -phenanthroline (28), -benzene (29-30), and -thiophene (24) scaffolds. The anilines are further functionalized with amide (20), sulfonamide (18, 24), or urea (19, 21-23, 25-30) groups to provide capabilities such as anion selectivity for nitrate (30) and H 2 PO 4 − (26), water solubility (25) or metal coordination (27). An example of a pyridine receptor with sulfonamide arms (e.g., 1 ) is shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Anion-directed self-assembly of a 2,6-bis(2-anilinoethynyl)pyridine bis(amide) scaffold

Tresca

Berryman

Zakharov

et al. 2016

Supramolecular Chemistry

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Bis(sulfonamide) receptors based on the 2,6-bis(2-anilinoethynyl)pyridine scaffold form persistent dimers with water and halides in solution and in the solid-state. The structurally related bis(amide) receptor derived from 3,5-dinitrobenzoyl chloride is a dimer in the solid-state with two HCl molecules directing the self-assembly. The 2+2 dimer, with a twisted “S”-shaped backbone, is held together by six hydrogen bonds. Dissolution of the (H2+·Cl−)2 adduct in CHCl3 results, however, in a monomeric structure. DOSY and 1H NMR experiments were used to identify the dominance of monomer in solution for both 2 and H2+·Cl−. The ‘OFF-ON’ fluorescence response of 2, 6-bis(2-anilinoethynyl)pyridine is retained with amide arms.

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Selective Nitrate Binding in Competitive Hydrogen Bonding Solvents: Do Anion–π Interactions Facilitate Nitrate Selectivity?

Cited by 75 publications

References 41 publications

“Off-on” aggregation-based fluorescent sensor for the detection of chloride in water

“Off-on” aggregation-based fluorescent sensor for the detection of chloride in water

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Anion-directed self-assembly of a 2,6-bis(2-anilinoethynyl)pyridine bis(amide) scaffold

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