title: An exclusive fluoride receptor: Fluoride-induced proton transfer to a quinoline-based thiourea.
abstract: A new quinoline-based tripodal thiourea has been synthesized, which exclusively binds fluoride anion in DMSO, showing no affinity for other anions including, chloride, bromide, iodide, perchlorate, nitrate and hydrogen sulfate. As investigated by1H NMR, the receptor forms both 1:1 and 1:2 complex yielding the binding constants of 2.32(3) (in logβ1) and 4.39(4) (in logβ2), respectively; where quinoline groups are protonated by the fluoride-induced proton transfer from the solution to the host molecule. The 1:2 binding is due to the interactions of one fluoride with NH binding sites of urea sites and another fluoride with secondary+NH binding sites within the tripodal pocket. The formation of both 1:1 and 1:2 complexes has been confirmed by the theoretical calculations based on density functional theory (DFT).
authors.affiliation: Department of Chemistry, Balikesir University, 10145, Balikesir, Turkey.
authors.forename: Ismet
authors.initials: I
authors.lastname: Basaran
authors.affiliation: Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39212, USA.
authors.forename: Maryam Emami
authors.initials: ME
authors.lastname: Khansari
authors.affiliation: Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39212, USA.
authors.forename: Avijit
authors.initials: A
authors.lastname: Pramanik
authors.affiliation: Department of Chemistry and Department of Materials Science & Engineering, Drexel University, Philadelphia, PA 19104, USA.
authors.forename: Bryan M
authors.initials: BM
authors.lastname: Wong
authors.affiliation: Department of Chemistry, Balikesir University, 10145, Balikesir, Turkey.
authors.forename: Alamgir
authors.initials: A
authors.lastname: Hossain
keywords: Acyclic receptor; Anion complex; Fluoride sensor; Molecular recognition; Thiourea
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