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Supramolecular Sensing with Phosphonate Cavitands

Authors

  • Monica Melegari Dr.,

    1. Dipartimento di Chimica Organica ed Industriale and Unità INSTM, UdR Parma, Università degli Studi di Parma, Viale G.P. Usberti 17/a, 43100 Parma (Italy), Fax: (+39) 0521-905-472
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  • Michele Suman Dr.,

    1. Dipartimento di Chimica Organica ed Industriale and Unità INSTM, UdR Parma, Università degli Studi di Parma, Viale G.P. Usberti 17/a, 43100 Parma (Italy), Fax: (+39) 0521-905-472
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  • Laura Pirondini Dr.,

    1. Dipartimento di Chimica Organica ed Industriale and Unità INSTM, UdR Parma, Università degli Studi di Parma, Viale G.P. Usberti 17/a, 43100 Parma (Italy), Fax: (+39) 0521-905-472
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  • Davide Moiani Dr.,

    1. Dipartimento di Chimica Organica ed Industriale and Unità INSTM, UdR Parma, Università degli Studi di Parma, Viale G.P. Usberti 17/a, 43100 Parma (Italy), Fax: (+39) 0521-905-472
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  • Chiara Massera Dr.,

    1. Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università degli Studi di Parma, Viale G.P. Usberti 17/a, 43100 Parma (Italy)
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  • Franco Ugozzoli Prof.,

    1. Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università degli Studi di Parma, Viale G.P. Usberti 17/a, 43100 Parma (Italy)
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  • Elina Kalenius Dr.,

    1. Department of Chemistry, University of Joensuu, P.O. Box 111, 80101 Joensuu (Finland)
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  • Pirjo Vainiotalo Prof.,

    1. Department of Chemistry, University of Joensuu, P.O. Box 111, 80101 Joensuu (Finland)
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  • Jean-Christophe Mulatier,

    1. Laboratorie de Chimie, École Normale Supérieure de Lyon, CNRS, 46 Allée d'Italie, 69364 Lyon 07 (France)
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  • Jean-Pierre Dutasta Dr.,

    1. Laboratorie de Chimie, École Normale Supérieure de Lyon, CNRS, 46 Allée d'Italie, 69364 Lyon 07 (France)
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  • Enrico Dalcanale Prof.

    1. Dipartimento di Chimica Organica ed Industriale and Unità INSTM, UdR Parma, Università degli Studi di Parma, Viale G.P. Usberti 17/a, 43100 Parma (Italy), Fax: (+39) 0521-905-472
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Abstract

Phosphonate cavitands are an emerging class of synthetic receptors for supramolecular sensing. The molecular recognition properties of the third-generation tetraphosphonate cavitands toward alcohols and water at the gas–solid interface have been evaluated by means of three complementary techniques and compared to those of the parent mono- and diphosphonate cavitands. The combined use of ESI-MS and X-ray crystallography defined precisely the host–guest association at the interface in terms of type, number, strength, and geometry of interactions. Quartz crystal microbalance (QCM) measurements then validated the predictive value of such information for sensing applications. The importance of energetically equivalent multiple interactions on sensor selectivity and sensitivity has been demonstrated by comparing the molecular recognition properties of tetraphosphonate cavitands with those of their mono- and diphosphonate counterparts.

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