Organic Chemistry

Guest-induced misfolding of a crown-ether-functionalized ortho-phenylene

Authors

Abstract

A crown-ether-functionalized o-phenylene tetramer has been synthesized and co-assembled with monotopic and ditopic, achiral and chiral secondary ammonium ion guests. NMR spectroscopy shows that the o-phenylene forms both 1:1 and 1:2 complexes with monotopic guests while remaining well-folded. Binding of an elongated ditopic guest, however, forces the o-phenylene to misfold by pulling the terminal rings apart. A chiral ditopic guest biases the o-phenylene twist sense.

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Supplementary material

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Supporting information for "Guest-induced misfolding of a crown-ether-functionalized ortho-phenylene"
Supplemental figures, NMR spectra, UV-vis and CD spectra, computational chemistry data