Synthesis and self-assembly of functionalized donor-σ-acceptor molecules

3,5,7-Tris(arylmethyl)-1-aza-adamantanetrione donor-alpha-acceptor compounds have been synthesized in four steps. Computational and H-1 NMR analyses rationalize the solubility, gelation, and conformational properties of the C-3-symmetric molecules toward employing sigma-coupled donor-acceptor interactions in molecular self-assembly.