The interplay between aromaticity and hydrogen bonding in the self-assembly of squaramide-based supramolecular polymers is explored. Partially aromatic bis(squaramide) bolaamphiphiles were designed to self-assemble through a combination of hydrophobic, hydrogen-bonding and aromatic effects into high aspect ratio fibrils. Strong hydrogen bonding and aromatic gain of the monomer was observed using a combination of experimental (UV-vis, IR) and computational (NICS, HOMA) techniques. A significant increase in thermodynamic stability and a striking difference in the morphology of the self-assembled bis(squaramide) bolamphiphiles was observed in comparison to isosteres that cannot access the aromatic gain-hydrogen bonding effect. We have further examined the effect of modulating the hydrogen-bonding strength of the bolaamphiphilic monomer by using thionated squaramides; significant differences in the self-assembly behaviour of the monomers are observed.

Probing hydrogen bond-aromaticity coupling in squaramide-based supramolecular polymers

253rd National Meeting (2017)

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