1,2,3-Triazole-strapped calix[4]pyrrole: a new membrane transporter for chloride

Fisher, Matthew G.; Gale, Philip A.; Hiscock, Jennifer R.; Hursthouse, Michael B.; Light, Mark E.; Schmidtchen, Franz P.; Tong, Christine C.

doi:10.1039/b904089g

Cited by 132 publications

(46 citation statements)

References 35 publications

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“…[9] These include use of modified resorcinarenes, [4] strapped calix [4]pyrroles, [10] electron-deficient receptors, [3,11] and when using 1,2,3-triazoles [12] in macrocyclic triazolophanes, [5] foldamers [6] and other receptors. [13] Predictions and insights about the CÀH···anion bond have been provided by gas-phase calculations on substituted aryls [14][15][16] and on strapped calix [4]pyrroles. [10] In the former, phenyl CH···anion bonds are calculated to be~50 % the strength of pyrrole NH donors; however, anion polarization is believed to contribute to the overestimation of this interaction.…”

Section: Introductionmentioning

confidence: 99%

Strong CH⋅⋅⋅Halide Hydrogen Bonds from 1,2,3‐Triazoles Quantified Using Pre‐Organized and Shape‐Persistent Triazolophanes

Bandyopadhyay¹,

Raghavachari²,

Flood³

2009

ChemPhysChem

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The structures associated with halide (F-, Cl-, Br-) complexation inside CH hydrogen-bonding macrocyclic receptors, called triazolophanes, are characterized using density functional theory (DFT). The associated binding energies in the gas and solution phases are evaluated. The ruffles in the empty triazolophane become smoothed-out upon Cl(-)- and Br(-)-ion binding directly into the middle of the cavity. The largely pre-organized cavity morphs into an elliptical shape to facilitate shorter hydrogen bonds in the north and south regions and longer ones west and east. The smaller F- ion sits in, and flattens-out, only the north (or south) region. The 1,2,3-triazoles show shorter CH...Cl- contacts than for the phenylenes. Both Cl- and Br- show the same binding geometries but Cl- has a larger binding energy consistent with its stronger Lewis basicity. Model triads were used to decompose the overall binding energy into those of its components. In the course of this triad analysis, anion polarization was identified and its contribution to the triad...Cl- binding energy estimated. Consequently, the binding energies for the individual aryl units within the comparatively non-polarized triazolophanes were estimated. The 1,2,3-triazoles are twice as strong as the phenylenes thus contributing most of the interaction energy to Cl(-)-ion binding. Therefore, the 1,2,3-triazoles appear to approach the hydrogen bond strengths of the NH donors of pyrrole units.

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Section: Introductionmentioning

confidence: 99%

Strong CH⋅⋅⋅Halide Hydrogen Bonds from 1,2,3‐Triazoles Quantified Using Pre‐Organized and Shape‐Persistent Triazolophanes

Bandyopadhyay¹,

Raghavachari²,

Flood³

2009

ChemPhysChem

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“…This hypothesis is supported by evidence from a variety of solid-state structures showing cation inclusion in the calix[4]pyrrole cup 6. It has also been shown that calixpyrroles can extract metal salts from aqueous solution7 and transport caesium chloride salts across lipid bilayer membranes 8…”

Section: Introductionmentioning

confidence: 81%

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

et al. 2010

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“…Under these conditions, chloride was again released from the vesicles, thus ruling out a potential chloride nitrate antiport mechanism and confirming the caesium chloride co-transport process (Scheme 12). Gale and co-workers continued their studies on the membrane transport properties of calix [4]pyrroles and synthesized the strapped system 66 which contains a 1,2,3-triazole group [82]. Triazole groups have been shown by Flood and others to be excellent hydrogen bond donor groups for complexing anionic guests [83][84][85].…”

Section: Extraction and Transportmentioning

confidence: 97%

Calix[n]pyrroles as Anion and Ion-Pair Complexants

Gale

Lee

2010

Topics in Heterocyclic Chemistry

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This chapter covers advances in calixpyrrole chemistry and specifically in the application of these species as anion and ion-pair complexation agents over the last 5 years. Over this time, the chemistry of these easy-to-make macrocycles advanced with the discovery of the ion-pair complexation properties of calixpyrroles, in addition to the development of strapped calixpyrroles that incorporate extra hydrogen bond donors and possess higher affinities for anions than the parent macrocycle. Calixpyrroles have also been employed as anion complexants in solvent-solvent extraction and in polymers. They have also been shown to function as lipid bilayer transport agents for salts and as organocatalysts.

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1,2,3-Triazole-strapped calix[4]pyrrole: a new membrane transporter for chloride

Cited by 132 publications

References 35 publications

Strong CH⋅⋅⋅Halide Hydrogen Bonds from 1,2,3‐Triazoles Quantified Using Pre‐Organized and Shape‐Persistent Triazolophanes

Strong CH⋅⋅⋅Halide Hydrogen Bonds from 1,2,3‐Triazoles Quantified Using Pre‐Organized and Shape‐Persistent Triazolophanes

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

Calix[n]pyrroles as Anion and Ion-Pair Complexants

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