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Article Dans Une Revue Chemistry - A European Journal Année : 2016

Straightforward and Controlled Shape Access to Efficient Macrocyclic Imidazolylboronium Anion Receptors

Résumé

Straightforward synthesis of air- and waterstable bis-cationic macrocyclic imidazolylboronium anion receptors is described herein. By taking advantage of the bulky and rigid 9-borabicyclo[3.3.1]-nonane (9-BBN) attaching point and a well-designed bis-imidazolylaryl, highly stable dimeric imidazolylboronium macrocycles were synthesized. Additionally, NMR spectroscopy ( 1H, DOSY, and HOESY), mass spectrometry (MS), and X-ray diffraction studies revealed that these macrocyclic scaffolds can bind several monoanions with high association constants in DMSO, and are particularly sensitive for the MS detection of anions (with concentrations in the nm range). This anion/receptor interaction involves eight C-H binding sites, which include Csp2-H and unusual Csp3-H hydrogen-bonding donors.

Dates et versions

hal-01415222 , version 1 (12-12-2016)

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Citer

Momar Toure, Laurence Charles, Christophe Chendo, Viel Stéphane, Olivier Chuzel, et al.. Straightforward and Controlled Shape Access to Efficient Macrocyclic Imidazolylboronium Anion Receptors. Chemistry - A European Journal, 2016, 22 (8937-8942), ⟨10.1002/chem.201601174⟩. ⟨hal-01415222⟩
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