The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n–cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.

Capitalizing on our experience in constructing branched and dendritic monomers with functionalizable aromatic moiety at the focal point and various terminal groups, we prepared lipophilic and water-soluble dendrimers with BODIPY fluorophore in the core, emitting in the green and near IR spectral regions. The dendrimers, incorporating aliphatic tails, exhibited excellent fluorescence properties in apolar organic solvents, while those with the triethylenglycol-based tails were highly fluorescent in polar organic solvents as well. The water solubility induced by the terminal hexaethyleneglycol tails enables fluorescence of the dyes also in aqueous media. The phenolic hydroxyls in the molecules enable attachment of linkers for prospective conjugation of additional units.