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Original Articles

Monopyrrolotetrathiafulvalenium dication and its complexation with 1,5-dinaphtho[38]crown-10

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Pages 157-163 | Received 21 Aug 2008, Accepted 13 Oct 2008, Published online: 14 Dec 2010
 

Abstract

The synthesis and characterisation of a monopyrrolotetrathiafulvalene dication 1 2+, isolated both as its perchlorate (ClO4 − ) and hexachloroantimonate (SbCl6 ) salt, is described. The complexation between the π-electron acceptor 1 2+ and the π-electron donating macrocyclic polyether 1,5-dinaphtho[38]crown-10 (1/5DN38C10) has been investigated using 1H NMR spectroscopy and a binding constant (K a) of 3.7 ± 0.3 × 102 M–1 was obtained for the 1 2+ ⊂ 1/5DN38C10 complex (as its perchlorate salt) in acetonitrile at 298 K. The results reveal that the strength of the binding between 1 2+ and 1/5DN38C10 is one order of magnitude smaller than that for the binding between the parent tetrathiafulvalene (TTF) dication (i.e. TTF2+) and 1/5DN38C10.

Acknowledgements

We gratefully acknowledge financial support provided by the Danish Natural Science Research Council through the SONS Programme of the European Science Foundation, which is also funded by the European Commission, Sixth Framework Programme and the Strategic Research Council (Project #2117-05-0115) in Denmark.

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