A naphthalene-barbiturate conjugant (G-Np) and a pockety barbiturate receptor (Hamilton receptor, H-receptor) with two 2,6-diaminopyridine groups linked through an isophthalic acid spacer were synthesized. The dyad is created by functionalizing the H-receptor and G-Np with six hydrogen bonds, which provide a high apparent association constant (KAPP approximately equal to (4.9±0.5)×104 mol－1•L in CH2Cl2). Excitation with 330 nm light mainly results in a singlet electron transfer between naphthalene and the H-receptor at room temperature, and a triplet energy transfer from the H-receptor to naphthalene at 77 K. These findings provide a new model for the study of the Hamilton hydrogen-bonded system, and will benefit understanding the role of hydrogen bonding in natural assemblies.

Key words: hydrogen bond, Hamilton receptor, photoinduced electron transfer, triplet energy transfer