Diaminoterephthalate-α-lipoic acid conjugates with fluorinated residues.

ABSTRACT: Two bifunctional diaminoterephthalate (DAT) fluorescence dyes were prepared in a three-step sequence including one deprotection reaction. One functional unit is α-lipoic acid (ALA) for binding the dye to gold surfaces. It was introduced to the DAT scaffold by an amidation reaction. The other functional unit is a para-(trifluoromethyl)benzyl group for facile detection of the surface-bound material by X-ray photoelectron spectroscopy (XPS). This residue was introduced by reductive amination of the DAT scaffold with the respective benzaldehyde derivative. In one compound (60% yield over three steps) the ALA unit is directly bound to the DAT as a relatively electron-withdrawing amide. In solution (CH₂Cl₂), this material shows strong fluorescence (quantum yield 57%

SUBMITTER: Buschbeck L 

PROVIDER: S-EPMC6541350 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature