Interactions of a water-soluble calix[4]arene with spermine: solution and solid-state characterisation

Alessandro D’Urso, Giovanna Brancatelli, Neal Hickey, Erica Farnetti, Rita De Zorzi, Carmela Bonaccorso, Roberto Purrello, Silvano Geremia

Research output: Contribution to journalArticlepeer-review

Abstract

The octaanionic 5,11,17,23-tetrasulfonato-25,26,27,28-tetrakis(hydroxycarbonylmethoxy)-calix[4]arene (cone conformation) (C4TsTc) was investigated as a sensor for the biogenic tetracationic polyamine, spermine .(H4Spe4+). Fluorescence titration experiments of the water-soluble calixarene with spermine showed the formation of the 2:1 and 1:1 calixarene:spermine complexes in solution. The single crystal X-ray diffraction analysis of [(NaC4TsTc)4·(H4Spe)7] confirmed the formation of 2:1 and 1:1 calixarene:spermine species and showed that the water-soluble calixarene binds the spermine either by partially hosting it in the inner cavity or through the carboxylate groups on the lower rim. In order to investigate the effect of multivalent systems, supramolecular assemblies of octaanionic calixarene molecules templated by meso-tetrakis(4-N-methylpyridyl)porphyrin (H2T4) in different stoichiometric porphyrin:calixarene ratios (1:4 and 3:4) were also tested for spermine binding in solution. Fluorescence titration experiments with the 1:4 and 3:4 H2T4:C4TsTc supramolecular complexes showed that the multivalent assemblies are more sensitive to the presence of spermine than the calixarene alone.

Original languageEnglish
Pages (from-to)1-7
Number of pages7
JournalSupramolecular Chemistry
DOIs
Publication statusAccepted/In press - Jan 13 2016

Keywords

  • calixarene
  • fluorescence titration
  • Spermine
  • supramolecular complexes
  • X-ray crystallography

ASJC Scopus subject areas

  • Chemistry(all)

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