Spectroscopic study on the intermolecular double proton transfer in 4-(naphthalen-1-yl)-6-octyl-1,3,5-triazin-2-amine with acid

With 2,4,6-trichloro-1,3,5-triazine as starting material, a functionalized triazine derivative, 4-(naphthalen-1-yl)-6-octyl-1,3,5-triazin-2-amine (NOTA) was synthesized in 14% yield through three steps: Kumada cross-coupling, Suzuki coupling and amination. Intermolecular double proton transfer of NOTA with acetic acid (HOAc) and trifluoroacetic acid (TFA) in chloroform was investigated by UV–vis absorption and fluorescence emission. It is found that both NOTA/HOAc and NOTA/TFA undergo excited state double proton transfer, resulting in amino–imino tautomerization emission in excited state.