Fine tuning the anion binding properties of 2,6-diamidopyridine dipyrromethane hybrid macrocycles

JL Sessler, E Katayev, GD Pantos, P Scherbakov, MD Reshetova, VN Khrustalev, VM Lynch, YA Ustynyuk

Research output: Contribution to journalArticle

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Abstract

The synthesis, characterization, and anion-binding properties of a series of 2,6-diamidopyridine dipyrromethane hybrid macrocycles is presented. As part of this work, a new method for effecting the oxidation of dipyrromethane-based macrocycles in organic solvents has been developed. The macrocyclic frameworks presented here stand out because of their ease of synthesis and tunable anion-binding properties. Evidence for anion binding was obtained from UV-vis spectroscopic titrations carried out in acetonitrile. The results clearly indicate that by changing the flexibility, cavity size, and directionality of anion-binding moieties in the macrocyclic framework the anion selectivity may be changed dramatically. These results are in accord with density functional theory molecular modeling calculations performed on one member of the series.
Original languageEnglish
Pages (from-to)11442-11446
Number of pages5
JournalJournal of the American Chemical Society
Volume127
Issue number32
DOIs
Publication statusPublished - 17 Aug 2005

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Anions
Negative ions
Tuning
Molecular modeling
Acetonitrile
Titration
Organic solvents
Density functional theory
diamidopyridine
dipyrromethane
Oxidation

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Sessler, JL., Katayev, E., Pantos, GD., Scherbakov, P., Reshetova, MD., Khrustalev, VN., ... Ustynyuk, YA. (2005). Fine tuning the anion binding properties of 2,6-diamidopyridine dipyrromethane hybrid macrocycles. Journal of the American Chemical Society, 127(32), 11442-11446. https://doi.org/10.1021/ja0522938

Fine tuning the anion binding properties of 2,6-diamidopyridine dipyrromethane hybrid macrocycles. / Sessler, JL; Katayev, E; Pantos, GD; Scherbakov, P; Reshetova, MD; Khrustalev, VN; Lynch, VM; Ustynyuk, YA.

In: Journal of the American Chemical Society, Vol. 127, No. 32, 17.08.2005, p. 11442-11446.

Research output: Contribution to journalArticle

Sessler, JL, Katayev, E, Pantos, GD, Scherbakov, P, Reshetova, MD, Khrustalev, VN, Lynch, VM & Ustynyuk, YA 2005, 'Fine tuning the anion binding properties of 2,6-diamidopyridine dipyrromethane hybrid macrocycles', Journal of the American Chemical Society, vol. 127, no. 32, pp. 11442-11446. https://doi.org/10.1021/ja0522938
Sessler, JL ; Katayev, E ; Pantos, GD ; Scherbakov, P ; Reshetova, MD ; Khrustalev, VN ; Lynch, VM ; Ustynyuk, YA. / Fine tuning the anion binding properties of 2,6-diamidopyridine dipyrromethane hybrid macrocycles. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 32. pp. 11442-11446.
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