This article presents the synthesis, the structural determination and the sensing capabilities toward Volatile Organic Compounds of a new class of fluorescent indolizine-cyclodextrin sensors. The synthesis of these sensors has been performed by two different pathways, both involving bipyridinium ylides and 6-amino-b-cyclodextrin. The sensors structures were dominantly established by 2D-NMR spectra and systematically represented by molecular modelling (MM3, AM1, AM1-COSMO methods). The sensing capabilities of the sensors were evaluated by fluorescence, during the inclusion of the guest (adamantanol or aromatic derivatives) into the cyclodextrin host cavity. The guest– host complex formation was controlled by formation constants determination, using experimental methods, coupled with theoretical formation energies calculation using a specific docking procedure. Both experimental and theoretical results recommend some compounds as very attractive sensors for VOCs detection. Other similar compounds could be taken in consideration as biological markers. The qualitative data obtained by the sensors towards VOC permits the extension of these experimental and theoretical techniques on other analogues inclusion phenomena with larger applied interest.
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