Design, Synthesis and Aggregation of Amphiphilic Monomers—Cyclic and Tubular Hydrogen‐Bonded Self‐assembly in Conventional and Polar Media

Two hydrogen‐bonding monomers containing tetraethylene glycol (TEG) chains have been synthesized and characterized. The monomers are based on a bicyclic scaffold appended with either 4H‐bonding benzyl‐substituted ureidopyrimidinone motifs or 2H‐bonding unsubstituted pyrrole‐fused ureidopyrimidinone motifs, with the TEG chains introduced with the aim of developing amphiphilic monomers soluble in nonpolar and polar organic solvents in order to extend the utility of H‐bonding in supramolecular chemistry. In CDCl 3 , both monomers formed cyclic tetramers. The monomer containing 2H‐bonding motifs was found to form significantly less‐stable aggregates than its previously reported alkylated analogue, most likely due to interference from the TEG chains. Despite the weaker aggregation, the 2H‐bonded tetramers were able to stack into tubular polymers through orthogonal H‐bonding in less polar solvent (toluene) or when a suitable guest (C 70 ) was introduced. Comparison of the TEGylated monomers with previously reported alkylated analogues showed that the introduction of TEG chains resulted in increased solubility in a wide range of solvents. By using one of the TEGylated monomers, nonpolar C 60 could be solubilized in polar solvent acetonitrile by forming an inclusion complex. This complex was used as a homogeneous catalyst for photochemical oxidation of sulfides to sulfoxides in acetonitrile.