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Chlorophyll and bacteriochlorophyll derivatives possessing a trifluoroacetyl group at the 3-position were synthesized as new colorimetric sensors for amine detection. α-Amino alcohol formation of the free-base chlorin and metallochlorins showed visual color changes from brown to purple and from green to blue, respectively. On the other hand, bacteriochlorin derivative showed large blue-shifts of the Qy peak in the near-infrared region (775 → 724 nm) and the Qx peak in the visible region (549 → 520 nm), which are advantageous points for amine sensing. Clear color change was observed from pink to turquoise by the formation of α-amino alcohol adduct.

3-Trifluoroacetylchlorin possessing an ω-aminoalkyl chain at the 17-propionate residue was prepared to realize a chlorophyll-based supramolecule acting as a thermochromic switch. A THF solution of the synthetic sensor molecule appeared brown, while the solution color became purple at lower temperature due to the conversion of the trifluoroacetyl group to its α-amino alcohol adduct form in a molecule.