Readily functionalized AAA–DDD triply hydrogen-bonded motifs

Herein we present a new, readily functionalized AAA-DDD hydrogen bond array. A novel AAA monomeric unit (3a-b) was obtained from a two-step synthetic procedure starting with 2-aminonicotinaldehyde via microwave radiation (overall yield of 52-66%). H-1 NMR and fluorescence spectroscopy confirmed the complexation event with a calculated association constant of 1.57 x 10(7) M-1. Likewise, the usefulness of this triple hydrogen bond motif in supramolecular polymerization was demonstrated through viscosity measurements in a crosslinked supramolecular alternating copolymer.