New Macrocyclic Ligands. Synthesis of an Extensive Series of Potentially Pentadentate Ligands Containing Mixed Nitrogen, Oxygen and or Sulfur Heteroatoms. The X-Ray Structure of an O2N2S Derivative

Baldwin, Darren S.; Duckworth, PA; Erickson, G. R.; Lindoy, L. F.; McPartlin, Mary; Mockler, Garry M.; Moody, W. E.; Tasker, PA

doi:10.1071/ch9871861

Cited by 36 publications

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“…The precursor dialdehyde and the corresponding macrocycle L were prepared using the previous reports. − The pyridine derivative of the dibenzodiaza-crown macrocycle, L py , was synthesized by the following method: the parent macrocycle L (1.00 g) was dissolved in DMF (10 mL) in the presence of potassium carbonate (1.12 g) and potassium iodide (0.03 g), before stirring the mixture of 1 with 4-chloromethyl pyridine hydrochloride (0.5 g) for 7 days under a N 2 atmosphere at RT. A brownish-color precipitate was separated after the addition of water (300 mL).…”

Section: Methodsmentioning

confidence: 99%

Selective Supramolecular Recognition of Nitroaromatics by a Fluorescent Metal–Organic Cage Based on a Pyridine-Decorated Dibenzodiaza-Crown Macrocyclic Co(II) Complex

2023

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Two isomorphous fluorescent (FL) lantern-shaped metal−organic cages 1 and 2 were prepared by coordinationdirected self-assembly of Co(II) centers with a new aza-crown macrocyclic ligand bearing pyridine pendant arms (L py ). The cage structures were determined using single-crystal X-ray diffraction analysis, thermogravimetric, elemental microanalysis, FT-IR spectroscopy, and powder X-ray diffraction. The crystal structures of 1 and 2 show that anions (Cl − in 1 and Br − in 2) are encapsulated within the cage cavity. 1 and 2 bear two coordinated water molecules that are directed inside the cages, surrounded by the eight pyridine rings at the "bottom" and the "roof" of the cage. These hydrogen bond donors, π systems, and the cationic nature of the cages enable 1 and 2 to encapsulate the anions. FL experiments revealed that 1 could detect nitroaromatic compounds by exhibiting selective and sensitive fluorescence quenching toward pnitroaniline (PNA), recommending a limit of detection of 4.24 ppm. Moreover, the addition of 50 μL of PNA and o-nitrophenol to the ethanolic suspension of 1 led to a significant large FL red shift, namely, 87 and 24 nm, respectively, which were significantly higher than the corresponding values observed in the presence of other nitroaromatic compounds. The titration of the ethanolic suspension of 1, with various concentrations of PNA (>12 μM) demonstrated a concentration-dependent emission red shift. Hence, the efficient FL quenching of 1 was capable of distinguishing the dinitrobenzene isomers. Meanwhile, the observed red shift (10 nm) and quenching of this emission band under the influence of a trace amount of o-and p-nitrophenol isomers also showed that 1 could discriminate between o-and p-nitrophenol. Replacement of the chlorido with a bromido ligand in 1 generated cage 2 which was a more electron-donating cage than 1. The FL experiments showed that 2 was partially more sensitive and less selective toward NACs than 1.

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Section: Methodsmentioning

confidence: 99%

Selective Supramolecular Recognition of Nitroaromatics by a Fluorescent Metal–Organic Cage Based on a Pyridine-Decorated Dibenzodiaza-Crown Macrocyclic Co(II) Complex

2023

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“…[1][2][3][4][5] Mixed-donor macrocycles incorporating nitrogen together with oxygen and/or sulfur donors have been reported, and their interactions with a range of metal ions have been investigated. [6][7][8][9][10][11] One of the most important applications of such macrocycles is the separation of specific metal ions, which has been developed using various methods through extensive investigations. [12][13][14][15][16] In those approaches, macrocyclic ligands are immobilized on insoluble organic supports (cross-linked polystyrene and condensation polymers) or silica gel.…”

Section: Introductionmentioning

confidence: 99%

“…A number of investigations involving the use of macrocyclic ligands for metal ion discrimination have been reported. − Mixed-donor macrocycles incorporating nitrogen together with oxygen and/or sulfur donors have been reported, and their interactions with a range of metal ions have been investigated. − …”

Section: Introductionmentioning

confidence: 99%

Selective Separation of Hg(II), Pt(II), and Pd(II) Ions Using Silica-Gel-Bound Macrocycles Incorporating O₂N₂- and O₃N₂-Donor Sets

Kim¹,

Han²,

Shim³

et al. 2001

Ind. Eng. Chem. Res.

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Silica-gel-bound macrocycles (SGBMs) incorporating O2N2- and O3N2-donor sets have been synthesized, and their binding properties and selective separations toward Sr(II), Cu(II), Rh(III), Hg(II), Pt(II), and Pd(II) ions in aqueous HCl solution have been investigated. All binding constants decreased with increasing acid concentration, and values for Hg(II), Pt(II), and Pd(II) ions were greater than those for Sr(II), Cu(II), and Rh(III) ions. Pt(II) and Pd(II) ions or Hg(II) ion were selectively separated on stationary phases using SGB-2 and SGB-3, and these results were in accordance with expectations from binding constants.

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“…As an extension of our previous investigations we now report a study of the latter type in which the 17-membered rings L'-L6 (ref. 5 ) have been used to investigate the effect of stepwise donor-set variation on silver(I)/lead(Ii) discrimination.…”

mentioning

confidence: 99%

Dalton communications. Metal-ion recognition. Donor-set control of silver(I)/lead(II) discrimination using mixed-donor macrocyclic ligands

Adam¹,

Baldwin²,

Bashall³

et al. 1994

J. Chem. Soc., Dalton Trans.

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New Macrocyclic Ligands. Synthesis of an Extensive Series of Potentially Pentadentate Ligands Containing Mixed Nitrogen, Oxygen and or Sulfur Heteroatoms. The X-Ray Structure of an O2N2S Derivative

Abstract: The syntheses of 16 new 16-to 19-membered dibenzo macrocycles are reported. These rings incorporate nitrogen together with oxygen andlor sulfur heteroatoms. The X-ray structure of the 17-membered macrocycle containing an 0 2 N 2 S heteroatom set is described.

Cited by 36 publications

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Selective Supramolecular Recognition of Nitroaromatics by a Fluorescent Metal–Organic Cage Based on a Pyridine-Decorated Dibenzodiaza-Crown Macrocyclic Co(II) Complex

Selective Supramolecular Recognition of Nitroaromatics by a Fluorescent Metal–Organic Cage Based on a Pyridine-Decorated Dibenzodiaza-Crown Macrocyclic Co(II) Complex

Selective Separation of Hg(II), Pt(II), and Pd(II) Ions Using Silica-Gel-Bound Macrocycles Incorporating O₂N₂- and O₃N₂-Donor Sets

Dalton communications. Metal-ion recognition. Donor-set control of silver(I)/lead(II) discrimination using mixed-donor macrocyclic ligands

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New Macrocyclic Ligands. Synthesis of an Extensive Series of Potentially Pentadentate Ligands Containing Mixed Nitrogen, Oxygen and or Sulfur Heteroatoms. The X-Ray Structure of an O2N2S Derivative

Abstract: The syntheses of 16 new 16-to 19-membered dibenzo macrocycles are reported. These rings incorporate nitrogen together with oxygen andlor sulfur heteroatoms. The X-ray structure of the 17-membered macrocycle containing an 0 2 N 2 S heteroatom set is described.

Cited by 36 publications

References 0 publications

Selective Supramolecular Recognition of Nitroaromatics by a Fluorescent Metal–Organic Cage Based on a Pyridine-Decorated Dibenzodiaza-Crown Macrocyclic Co(II) Complex

Selective Supramolecular Recognition of Nitroaromatics by a Fluorescent Metal–Organic Cage Based on a Pyridine-Decorated Dibenzodiaza-Crown Macrocyclic Co(II) Complex

Selective Separation of Hg(II), Pt(II), and Pd(II) Ions Using Silica-Gel-Bound Macrocycles Incorporating O2N2- and O3N2-Donor Sets

Dalton communications. Metal-ion recognition. Donor-set control of silver(I)/lead(II) discrimination using mixed-donor macrocyclic ligands

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Selective Separation of Hg(II), Pt(II), and Pd(II) Ions Using Silica-Gel-Bound Macrocycles Incorporating O₂N₂- and O₃N₂-Donor Sets