GAETA, CARMINE

NERI, Placido

PIERRO, TERESA

TROISI, FRANCESCO

English

Archivio della Ricerca - Università di Salerno

oItttlDo]DlDoItItft!tIt!ttoúttttoooa)aaaaatCalix2007, August 6-9,2007, College Park, MD, USARecognition and Switching PropeÉies of Galix[4]areneGarboxylate DerivativesT. Pieno, F. Troisi, C. Gaeta, and Placido Neri*D i p a ft i m e n to a i c n i m i c a, lluf,u;tiffí,r:Íl q F i s c i a n o, S a t e m o, I t a t ySince the initial reports,l calixarenes bearing carborylic groups at the upper rim have attractedthe attention of several research groups and, consequently, have then be used mainly asintermediate for the construction of more sophisticated structures possessing peculiarproperties.2 Unexpectedly, the recognition properties of these derivatives as such, or'of theircorresponding carboxylate anions have received very little attention probably because of thedetrimental dependence on the pH of the medium.However, we reasoned that this negative dependence can be turned to a positive property ifconsidered in the context of switching systems.3 Therefore, we have recently undertaken astudy aimed to investigate these aspects. Thus, we first studied some calix[4]arene dicarboxylicacid derivatives and their conesponding sodium salts (exemplified by f ).R = Methyl, n-Propyl, n-Pentyl2In this communication we will report on the synthesis of these derivatives and on their lH NMRtitration studies to evaluate their recognition properties toward guests bearing quaternarynitrogens, such as Paraquat (1,1'-dimethyil4,4'-dipyridinium dichloride, 2') and N-methylpyridinium 3. In addition, we will report on the binding mode of the complexes whichevidenced an induced fit effect in the callxarene host upon complexation.References1 van Loon, J.-D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungano, R.; Harkema, S.; Reinhoudt,D. N. J. org. chem. 1990, 55, 5639-5646. conner, M.; Janout, v.; Regen, s. L. J. org. chem. lgg2, s7,3744-3746. Larsen, M.; Jorgensen, M. J. Org. Chem.l996, 61, 6651-6655." casnati, A.; sansone, F.; Ungaro, R. Acc. chem. Res. 2003, 96, 246-2s4. yin, H.; Hamilton, A. D.Angew. Chem. lnt. Ed.2005, 44,41304163.'De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. p.; Rademacher, J.T.; Rice, T.E. Chem. Rev. 1997, 97, 1515-1566.Calix 2OO7 - http://www.chem.umd.edu/conferencesl calir2007 |P-71

Recognition and switching properties of calix[4]arene carboxylate derivatives

Calixarene carboxylate derivatives: cation recognition and switching properties

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Recognition and switching properties of calix[4]arene carboxylate derivatives

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Archivio della Ricerca - Università di Salerno

Archivio della Ricerca - Università di Salerno