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Demonstrates how altering side-chain polarity impacts aggregation and solubility in pyrene-functionalized cyclophanes, suggesting new pathways for material design.
We synthesized cyclophanes bearing a pyrene moiety through a hydrophilic linker composed of one or two consecutive PEG-amido group and investigated the effects of polarity of the side chains on water-solubility and aggregation behavior. Amphiphilic pyrene-functionalized cyclophanes bearing three hydrophobic Boc-protected β-alanine residues in the side chains underwent aggregation in water, as confirmed by DLS measurements, TEM observations, and fluorescence techniques based on a broad excimer emission band around 480 nm. In contrast, the introduction of three hydrophilic ammonium-containing side chains to the pyrene-appended cyclophanes led to water-solubility due to self-inclusion behavior, and only monomer emission was observed.
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Hayashida et al. (2026) studied this question.
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