Synthesis, Characterization, and Use of Lanthanide Chelate of βDiketonate Based Ligand as a Luminescent Biolabel

Abstract

In this study, we aimed to synthesize a β-diketonate-based ligand and its Eu(III) complexwhich are used for luminescent biolabel. For this purpose, we chose acetophenone as the startingmaterial which contains methyl group at the alpha position of the ketone group. Firstly, we obtained4,4,5,5,6,6,7,7-octafluoro-3,8-dihydroxy-1,10-diphenyldeca-2,8-diene-1,10-dione (H2ODIT) ligand in areaction between acetophenone and diethyloctafluoroadipate with Claisen condensation. This ligand wascharacterized by 1H-NMR, 13C-NMR, and mass spectral analyses. We obtained a single crystal H2ODIT ascharacterized by X-ray analysis. At the second step, in order to bind H2ODIT to the antibody, it isreacted with chlorosulfonic acid. As a result of this reaction, the functional group of -ClSO2 was bound tothe structure. The structure of H2CODIT was characterized by NMR and mass spectral analysis. In thethird step, to understand the usability of the ligand as a biolabel, the complex compound wassynthesized with EuCl3. The complex compound was excited with UV light at 306 nm wavelength,specific hypersensitive 5D0 → 7F2 phosphorescence electronic transition of the Eu(III) was observedwhich proved that the luminescent H2CODIT molecule can work as a biolabel.