title: Selective Fluorimetric Detection of Primary Alkylamines by a Calix[6]arene Funnel Complex.
abstract: The association of host-guest and coordination chemistry was used to develop a fluorescent molecular sensor. A calix[6]arene bearing three imidazole arms at the small rim and three quinoline fluorophores at the large rim was synthesized and characterized. A two-step coordination sequence was observed upon addition of ZnII. The first ZnIIcenter binds the tris-imidazole small rim site, leading only to a small perturbation of the fluorescence. In contrast, a large bathochromic shift is observed upon binding of the second ZnIIcenter at the large rim as a result of the direct interaction of ZnIIwith the quinoline fluorophores. The system acts as a selective receptor for primary amines. Host-guest adduct formation could be identified by a shift and enhancement of the fluorescence emission that is dependent on the length and shape of the primary amine. This system constitutes a fluorescent reporter with a selective response among primary amines.
authors.affiliation: PPSM, ENS Cachan, CNRS, Université Paris Saclay, 161 avenue du Président Wilson, 94235, Cachan Cedex, France.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Rémy
authors.affiliation: CNRS UMR 8601, Laboratoire de Chimie et de Biochimie pharmacologiques et toxicologiques, Université Paris Descartes, Sorbonne Paris Cité, 45 rue des Saints Pères, 75006, Paris, France.
authors.forename: Hélène
authors.initials: H
authors.lastname: Guyon
authors.affiliation: CNRS UMR 8601, Laboratoire de Chimie et de Biochimie pharmacologiques et toxicologiques, Université Paris Descartes, Sorbonne Paris Cité, 45 rue des Saints Pères, 75006, Paris, France.
authors.forename: Jean-Noël
authors.initials: JN
authors.lastname: Rebilly
authors.affiliation: PPSM, ENS Cachan, CNRS, Université Paris Saclay, 161 avenue du Président Wilson, 94235, Cachan Cedex, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Leray
authors.affiliation: CNRS UMR 8601, Laboratoire de Chimie et de Biochimie pharmacologiques et toxicologiques, Université Paris Descartes, Sorbonne Paris Cité, 45 rue des Saints Pères, 75006, Paris, France.
authors.forename: Olivia
authors.initials: O
authors.lastname: Reinaud
keywords: amine detection; calixarene; fluorescence; host-guest systems; quinoline