The strength and directionality of hydrogen bonds have made them very attractive in the engineering of supramolecular units. This has been translated to the design of multiple hydrogen-bond arrays in order to modify and tune the interaction between supramolecular building blocks. In the present work several bifunctionalized compounds equipped with 7-Amino-1H-[1,8]naphthyridin-2-one as DADA binding unit and a variation of linker moieties by including aromatic groups as benzene and naphthalene, heterocycles as 1,2,3-triazoles, and dendron moieties, by means of reactions as Glaser coupling, Sonogashira coupling and 1,3-dipolar cycloaddition, have been synthesized. Compounds with a dendron structure as linker exhibit adequate solubility in non-polar solvents to execute experiments to study their binding nature. 1H-NMR DOSY experiments suggested that the synthesized dendron compounds were present as dimers and trimers in deuterated dichloromethane.
