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

摘要

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.