Abstract
Covalently linked porphyrin–adenine (meso-5(4-(9-(2-oxyethyl)adenine)phenyl)-10,15,20-tritolylporphyrin, 1) and anthracene–thymine (1-(9-methylanthracene)thymine, 2) conjugates have been synthesized and fully characterized by elemental analysis, FAB mass, UV-vis, 1 H NMR, fluorescence and cyclic voltammetric methods. Detailed 1 H NMR studies reveal that 1 and 2 self-assemble in CDCl 3 solutions at 293 ± 3 K to form a two-point hydrogen-bonded, bichromophoric, supramolecular system 3 with a binding constant of 47 ± 5 M−1 and that both Hoogsteen- and Watson–Crick-type A–T assemblies exist in solution under these experimental conditions. Spectral and electrochemical data point out the possibility of occurrence of both energy and electron transfer reactions from the singlet excited state of 2 to 1 in the ensemble 3. The singlet state activity of the ensemble 3 has been probed mainly by the time-resolved fluorescence method and the results have been discussed in the light of those obtained earlier on similar ‘non-covalently’ or covalently bound bichromophoric systems.
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