Trifluoroacetyl-chlorin as a new chemosensor for alcohol/amine detection

Abstract

Chlorophyll derivative possessing a trifluoroacetyl group at the 3-position was synthesized as a new chemosensor for alcohols and amines. Intense Q y peak of the trifluoroacetyl-chlorin (701 nm in CHCl 3) showed blue shifts to 667 nm in MeOH and 665 nm in n-BuNH 2 due to the formation of the corresponding hemiacetal and hemiaminal with visible color changes. Thermodynamic parameters for the complexation between trifluoroacetyl-chlorin and n-BuNH 2 in CDCl 3 were determined to be Δ H = −48 kJ mol −1 and Δ S = −147 J K −1 mol −1. Ratiometric fluorescence sensing of n-BuNH 2 in THF was also demonstrated.