Organic Letters 2011-12-02

Self-assembly of dimeric tetrathiafulvalene-calix[4]pyrrole: receptor for 1,3,5-trinitrobenzene.

Kent A Nielsen, Paul C Stein

Index: Org. Lett. 13(23) , 6176-9, (2011)

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Abstract

The synthesis and binding properties of a tetrathiafulvalene (TTF)-calix[4]pyrrole receptor 2 appended with one 3,5-dinitrobenzoate guest moiety are reported. The preliminary studies revealed that the receptor is self-complexing into a dimer receptor 2•2. The self-complexation of the receptor leads to preorganization--in its 1,3-alternate conformation--and as a result hereof, the dimer receptor 2•2 is displaying a 2 order higher binding affinity toward analytes (e.g., 1,3,5-trinitrobenzene) than the model tetrathiafulvalene (TTF)-calix[4]pyrrole receptor 3.