Paper
Tetra-TTF calix[4]pyrrole: a rationally designed receptor for electron-deficient neutral guests.
Published Nov 19, 2004 · K. Nielsen, Won-seob Cho, J. Jeppesen
Journal of the American Chemical Society
138
Citations
2
Influential Citations
Abstract
A calix[4]pyrrole incorporating four appended tetrathiafulvalene (TTF) units has been synthesized, and its receptor abilities toward neutral electron-deficient guests, such as 1,3,5-trinitrobenzene, tetrafluoro-p-benzoquinone, and tetrachloro-p-benzoquinone, have been studied in solution by UV-vis and 1H NMR spectroscopies as well as in the solid-state by X-ray crystallography. In its 1,3-alternate conformation a 1:2 sandwich-like complex-stabilized by charge transfer and hydrogen bonding interactions-is formed between the tetra-TTF calix[4]pyrrole and the guest molecules. However, upon addition of chloride ions to the complex the 1,3-alternate conformation is changed in favor of a cone conformation which serves to effect a release of the guests from the tetra-TTF calix[4]pyrrole.
The tetra-TTF calix[4]pyrrole effectively binds and releases neutral electron-deficient guests, offering potential for targeted drug delivery.
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