title: Straightforward and Controlled Shape Access to Efficient Macrocyclic Imidazolylboronium Anion Receptors.
abstract: A straightforward synthesis of air- and water-stable 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 ((1) H, 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.
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Momar
authors.initials: M
authors.lastname: Toure
authors.affiliation: Aix Marseille Université, CNRS, ICR UMR 7273, 13397, Marseille, France.
authors.forename: Laurence
authors.initials: L
authors.lastname: Charles
authors.affiliation: Aix Marseille Université, CNRS, ICR UMR 7273, 13397, Marseille, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Chendo
authors.affiliation: Aix Marseille Université, CNRS, ICR UMR 7273, 13397, Marseille, France.|Institut Universitaire de France, 75005, Paris, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Viel
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France. olivier.chuzel@univ-amu.fr.
authors.forename: Olivier
authors.initials: O
authors.lastname: Chuzel
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France. jl.parrain@univ-amu.fr.
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Parrain
mesh_terms: D000838:Anions / Q000737:chemistry; D001665:Binding Sites; D001896:Boron Compounds / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000838:Anions; D001896:Boron Compounds; D047028:Macrocyclic Compounds; C004267:9-borabicyclo(3,3,1)nonane; D002244:Carbon; D006859:Hydrogen
keywords: NMR spectroscopy; anion receptors; boronium cations; hydrogen bonds; macrocycles