Abstract 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.
Hayashida et al. (Wed,) studied this question.