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• W1999627042 abstract "The ortho-phenylenes are a simple class of foldamers, with the formation of helices driven by offset aromatic stacking interactions parallel to the helical axis. For the majority of reported o-phenylene oligomers, the perfectly folded conformer comprises perhaps 50–75% of the total population. Given the hundreds or thousands of possible conformers for even short oligomers, this distribution represents a substantial bias toward the folded state. However, “next-generation” o-phenylenes with better folding properties are needed if these structures are to be exploited as functional units within more complex architectures. Here, we report several new series of o-phenylene oligomers, varying both the nature and orientation of the substituents on every repeat unit. The conformational behavior was probed using a combination of NMR spectroscopy, DFT calculations, and X-ray crystallography. We find that increasing the electron-withdrawing character of the substituents gives oligomers with substantially improved folding properties. With moderately electron-withdrawing groups (acetoxy), we observe >90% of the perfectly folded conformer, and stronger electron withdrawing groups (triflate, cyano) give oligomers for which misfolded states are undetectable by NMR. The folding of these oligomers is only weakly solvent-dependent. General guidelines for the assessment of o-phenylene folding by NMR and UV–vis spectroscopy are also discussed." @default.
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• W1999627042 date "2014-11-17" @default.
• W1999627042 modified "2023-10-18" @default.
• W1999627042 title "Enhanced Helical Folding of <i>ortho</i>-Phenylenes through the Control of Aromatic Stacking Interactions" @default.
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• W1999627042 doi "https://doi.org/10.1021/ja509902m" @default.
• W1999627042 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25373325" @default.
• W1999627042 hasPublicationYear "2014" @default.
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