Benzothiazol picolin/isonicotinamides molecular switches: Expectations and reality

The ground state tautomerism and excited state intramolecular proton transfer in two new molecular switches, namely N-(benzo[d]thiazol-2-yl)picolinamide and N-(benzo[d]thiazol-2-yl)isonicotinamide, are studied in acetonitrile by the combined use of steady state and time dependent spectroscopy and DFT calculations. Although, according to the theoretical calculations, two potential switching pathways are possible in N-(benzo[d]thiazol-2-yl)picolinamide, either through the pyridine or through the benzothiazole moiety, the experimental results show the same photodynamics as in N-(benzo[d]thiazol-2-yl)isonicotinamide. This indicates that the excited state proton transfer from the amide NH to the betzothiazole nitrogen is preferred in both compounds.

The original article in The Journal of Molecular Liquids here.

 

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