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

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.