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Interplay Between Cyclization and Polymerization in Ditopic Cavitand Monomers

Francesca Tancini ^A , Enrico Rampazzo ^B and Enrico Dalcanale ^A ^C

+ Author Affiliations

- Author Affiliations

^A Dipartimento di Chimica Organica e Industriale, Università di Parma, and INSTM UdR Parma, 43100 Parma, Italy.

^B Dipartimento ‘G. Ciamician’, Università di Bologna, 40126 Bologna, Italy.

^C Corresponding author. Email: enrico.dalcanale@unipr.it

Australian Journal of Chemistry 63(4) 646-652 https://doi.org/10.1071/CH09630
Submitted: 5 December 2009 Accepted: 1 February 2010 Published: 8 April 2010

Abstract

Quinoxaline kite velcrands were functionalized with a ureidopyrimidone moiety at the lower rim, in order to combine multiple hydrogen bonding and solvophobic interactions to build dual-coded supramolecular structures. The orthogonality of the selected binding motifs has been demonstrated by NMR studies, as well as the reversible nature of the obtained assemblies. At low concentration, the presence of a ring-chain equilibrium has been established by ¹H NMR experiments, and confirmed by static and dynamic light scattering measurements.

Acknowledgement

Financial support from INSTM to F.T. is gratefully acknowledged. This work was supported by the EU through the project BION (ICT 213219). We thank the Centro Interfacoltà di Misure ‘G. Casnati’ of the University of Parma for the use of NMR and HR-ESI-MS facilities.

References

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