Supramolecular sensing with phosphonate cavitands

Monica Melegari; Michele Suman; Laura Pirondini; Davide Moiani; Chiara Massera; Franco Ugozzoli; Elina Kalenius; Pirjo Vainiotalo; Jean Christophe Mulatier; Jean Pierre Dutasta; Enrico Dalcanale

doi:10.1002/chem.200800327

Supramolecular sensing with phosphonate cavitands

Monica Melegari, Michele Suman, Laura Pirondini, Davide Moiani, Chiara Massera, Franco Ugozzoli, Elina Kalenius, Pirjo Vainiotalo, Jean Christophe Mulatier, Jean Pierre Dutasta, Enrico Dalcanale

Research output: Contribution to journal › Article › peer-review

69 Scopus citations

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.

Original language	English (US)
Pages (from-to)	5772-5779
Number of pages	8
Journal	Chemistry - A European Journal
Volume	14
Issue number	19
DOIs	https://doi.org/10.1002/chem.200800327
State	Published - Jun 27 2008
Externally published	Yes

Keywords

Cavitands
Host-guest chemistry
Mass spectrometry
Molecular recognition
Sensors

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.200800327

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title = "Supramolecular sensing with phosphonate cavitands",

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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author = "Monica Melegari and Michele Suman and Laura Pirondini and Davide Moiani and Chiara Massera and Franco Ugozzoli and Elina Kalenius and Pirjo Vainiotalo and Mulatier, {Jean Christophe} and Dutasta, {Jean Pierre} and Enrico Dalcanale",

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day = "27",

doi = "10.1002/chem.200800327",

language = "English (US)",

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T1 - Supramolecular sensing with phosphonate cavitands

AU - Melegari, Monica

AU - Suman, Michele

AU - Pirondini, Laura

AU - Moiani, Davide

AU - Massera, Chiara

AU - Ugozzoli, Franco

AU - Kalenius, Elina

AU - Vainiotalo, Pirjo

AU - Mulatier, Jean Christophe

AU - Dutasta, Jean Pierre

AU - Dalcanale, Enrico

PY - 2008/6/27

Y1 - 2008/6/27

N2 - 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.

AB - 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.

KW - Cavitands

KW - Host-guest chemistry

KW - Mass spectrometry

KW - Molecular recognition

KW - Sensors

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DO - 10.1002/chem.200800327

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SN - 0947-6539

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EP - 5779

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 19

ER -

Supramolecular sensing with phosphonate cavitands

Abstract

Keywords

ASJC Scopus subject areas

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