Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

Abstract

The 2,5‐diaminoterephthalate (DAT) structural motif is a powerful chromophore with remarkable fluorescence properties. Containing two carboxylate and two amino groups, it defines a colored molecular scaffold that allows for orthogonal functionalization with up to four different functional units. These compounds can be accessed in a remarkably simple fashion through reactions of succinyl succinates with amines, followed by aerobic oxidation, which is, from a preparative point of view, an issue of paramount importance. Even though DATs have been known since the beginning of the last century, compared to other classes of dyes they are so far underrated in the literature. This review highlights applications in life sciences and materials science. Equipped with maleimides and cyclooctyne moieties, for example, the chromophore can be covalently conjugated to biomolecules, which allows for the study of protein conformations and protein–protein interactions. In some cases, DATs serve as “turn‐on” probes, because their fluorescence quantum yields are increased by orders of magnitude upon reaction with the molecular target. Additionally, DAT fluorophores exhibit efficient emission in the solid state. By choosing appropriate substituents at the amino and carboxylate moieties, the emission wavelengths can be tuned in a broad range. As nanocrystalline needles, for example, DATs can be applied as fluorescence antennas for plasmon polaritons on a gold surface.

Electron Transfer and Electron Excitation Processes in 2,5‐Diaminoterephthalate Derivatives with Broad Scope for Functionalization

“…Even though DATs have been known since the beginning of the last century, literature about them is limited compared to other classes of dyes. Interestingly, the DAT motif allows easy functionalization with up to four different effector units . This properties are attractive for application as a probe in life sciences and materials science .…”

“…Interestingly, the DAT motif allows easy functionalization with up to four different effector units . This properties are attractive for application as a probe in life sciences and materials science . These compounds are obtained by reactions of succinyl succinates with amines followed by aerobic oxidation …”

“…This properties are attractive for application as a probe in life sciences and materials science . These compounds are obtained by reactions of succinyl succinates with amines followed by aerobic oxidation …”

“…Monofunctionalized DATs have been reported as fluorescence sensor for hydrogen peroxide detection or as fluorescent probes covalently bound to proteins or other biomolecules . For example, the maleimide group can be used as functional group for the ligation of a thiol moiety at the surface of proteins .…”

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

“…Diaminoterephthalates (DATs) are powerful fluorescence dyes [1–2] with outstanding properties such as high quantum yields and pronounced stability against photobleaching [3–5]. Although being structurally relatively simple, this class of dyes is so far underrated in the literature.…”