Thymine and adenine derivatives with pyrene, tetrathiafulvalene and nitronyl nitroxide units: Synthesis and formation of ensembles sensing thymine and adenine molecules

Abstract

Four thymine (T) and adenine (A) derivatives with pyrene, tetrathiafulvalene and nitronyl nitroxide units (1, 2, 3 and 4) were synthesized and characterized. Fluorescent spectral studies indicate that the corresponding T and A derivatives can form ensembles with the association constant of ca. 104 L/mol. The ensemble of 1 and 2 shows pyrene excimer emission, while that of 1/3 and 2/4 displays rather weak fluorescence due to the “intramolecular” photoinduced electron transfer reactions. Addition of compounds 5 or 6, which is T and A derivatives, respectively, to the ensembles of 1/2, 1/3 and 2/4 results in reduction of excimer emission and enhancement of pyrene fluorescence. These results show that these ensembles are able to sense T and A molecules.