title: Fluorescent Indolizine-b-Cyclodextrin Derivatives for the Detection of Volatile Organic Compounds.
abstract: This paper presents the synthesis, the structural determination and the sensing capabilities toward Volatile Organic Compounds (VOCs) of a new class of fluorescent indolizine-cyclodextrin sensors. Two different pathways, both involving bipyridinium ylides and 6-amino-b-cyclodextrin, have been used to carry out the synthesis of these sensors. The macrocycle structures were dominantly established by ¹H-NMR spectra and systematically studied by molecular modelling (MM3, AM1, AM1-COSMO methods). The sensing capabilities of the sensors were evaluated by emission of fluorescence, during the inclusion of the guest (adamantanol or aromatic derivatives) into the cyclodextrin (CD) host cavity. The host/guest complex formation was investigated by formation constant determinations, using experimental methods, coupled with theoretical calculations of formation energies using a specific docking procedure. Both experimental and theoretical results suggest that some compounds would make very attractive sensors for VOC detection. Some compounds could also be taken into consideration as biological markers.
authors.affiliation: Laboratoire de Synthèse Organique et Environnement (EA 2599), 145 Avenue Maurice Schumann, 59140 Dunkerque, France.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Becuwe
authors.affiliation: Laboratoire de Synthèse Organique et Environnement (EA 2599), 145 Avenue Maurice Schumann, 59140 Dunkerque, France.
authors.forename: David
authors.initials: D
authors.lastname: Landy
authors.affiliation: Laboratoire de Synthèse Organique et Environnement (EA 2599), 145 Avenue Maurice Schumann, 59140 Dunkerque, France.
authors.forename: François
authors.initials: F
authors.lastname: Delattre
authors.affiliation: Laboratoire de Synthèse Organique et Environnement (EA 2599), 145 Avenue Maurice Schumann, 59140 Dunkerque, France.
authors.forename: Francine
authors.initials: F
authors.lastname: Cazier
authors.affiliation: Laboratoire de Synthèse Organique et Environnement (EA 2599), 145 Avenue Maurice Schumann, 59140 Dunkerque, France. lamotte@univ-littoral.fr.
authors.forename: Sophie
authors.initials: S
authors.lastname: Fourmentin
keywords: Indolizine-b-cyclodextrin; Volatile Organic Compounds; detection; docking; formation constants; sensing capabilities; sensor