Triaminotriazines - Photophysical investigations of a porphyrin-appended triazine receptor with a naphthalene diimide guest

Abstract

A modular synthetic approach to preparing a family of triaminotriazine receptors bearing porphyrin chromophores is described. The porphyrin-appended triaminotriazines are prepared in a stepwise manner employing either cyanuric chloride or fluoride and 5-(4′-aminophenyl)-10,15,20-triphenylporphyrin in the first step. Reaction of the porphyrintriazine with excess 1-pentylamine leads to a triazine core programmed for three-point hydrogen bonding. Addition of a complementary naphthalene diimide yields a supramolecular donor-acceptor dyad. Photophysical studies in CH2Cl2 solvent show efficient quenching of porphyrin fluorescence within the dyad, consistent with an electron transfer process. Copyr..