Concurrent and Mechanochemical Activation of Two Distinct and Latent Fluorophores via Retro-Diels-Alder Reaction of an Anthracene-Aminomaleimide Adduct.

Abstract

Generally, a typical mechanochromophore produces color change through chemical transformation into one or two identical new chromophores/fluorophores under applied mechanical force. Herein, we introduce a novel mechanophore based on an anthracene-aminomaleimide Diels-Alder (DA) adduct featuring two distinct and latent fluorophores. This nonfluorescent mechanophore undergoes retro-DA reaction upon mechanochemical activation in solution and the solid state, generating the respective anthracene and aminomaleimide fragments simultaneously, both of which are highly emissive with different fluorescent colors. In addition, the aminomaleimide fluorophore exhibits sensitive fluorescence on-off response to protic solvents or polar solvents, which enables dual-color mechanochromism from this single mechanophore.