Bifunctional Diaminoterephthalate Scaffolds as Fluorescence Turn‐On Probes for Thiols

The fluorescent diaminoterephthalate scaffold was equipped by amidation with three types of reactive functions: thiols for metal‐surface binding, alkynes for click reactions, and maleimides for ligation with proteins. Starting from a succinyl succinate derivative with two orthogonally cleavable ester functions, three monoamides (38–57 % yield over three steps) and two bisamides (19 and 25 % yield over five steps) were prepared. Although alkyne and thiol derivatized compounds showed reasonable luminescence behavior (Φ≈1–4 %), the fluorescence was quenched by the maleimide moiety. It was turned on (10‐ to 20‐fold increase of fluorescence quantum yield) by conjugate addition of thiols.