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...

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Bibliographic Details
Published in:Organic letters 2011-12, Vol.13 (23), p.6176-6179
Main Authors: Nielsen, Kent A, Stein, Paul C
Format: Article
Language:English
Subjects:
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Structure
Pyrroles - chemical synthesis
Pyrroles - chemistry
Trinitrobenzenes - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2025586