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Issue 10, 2003
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Potentiometric studies of complexation properties of tetrafunctionalized resorcinarene-based cavitands

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Abstract

Resorcinarene-based cavitands functionalized with [–NH–C(O)–CH2–(Ph)2PO] (I), [–NH–C(O)–CH2–(EtO)2PO] (II), [–NH–C(S)–NHC(O)Ph] (III) and [–NH–C(O)–NHC(O)Ph] (IV) moieties have been characterized potentiometrically. Both P-containing cavitands (I and II) form very stable complexes (log βIL > 18) for most of the examined cations as determined with the segmented sandwich membrane method. The order of the stability constants was found to be: Eu3+ > UO22+ > Pb2+, Cd2+, Sr2+ and Cu2+. Much weaker complexation occurs in the case of compounds III and IV (log βIL < 10.6) and the order of the stability constants was: Eu3+ > Pb2+ > Cu2+ > Ag+ > UO22+ > Na+ > K+ for III and UO22+ > Cd2+ > Pb2+ > Eu3+Cu2+ > Na+ > Ag+ > K+ for IV. The response to representatives of various cation groups and the selectivity of polymeric membrane electrodes based on these compounds are presented. While cavitands functionalized with phosphine oxide or phosphonate moieties (I or II) exhibited the highest selectivity for UO22+ and Pb2+ and a pronounced discrimination of Ag+ ions, thioamide- (III) and amide-functionalized (IV) cavitands showed preferences for Ag+ and Pb2+ and reduced selectivity toward UO22+ ions. The correlation between the potentiometric selectivity and the ability of examined cavitands to form metal–ligand complexes is discussed.

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Publication details

The article was received on 06 May 2003, accepted on 30 Jun 2003 and first published on 26 Aug 2003


Article type: Paper
DOI: 10.1039/B305032G
New J. Chem., 2003,27, 1440-1445

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    Potentiometric studies of complexation properties of tetrafunctionalized resorcinarene-based cavitands

    E. Malinowska, Ł. Górski, D. Wojciechowska, M. M. Reinoso-García, W. Verboom and D. N. Reinhoudt, New J. Chem., 2003, 27, 1440
    DOI: 10.1039/B305032G

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