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Cd<sup>2+</sup>-Selective Fluorescence Enhancement of Bisquinoline Derivatives with 2-Aminoethanol Skeleton
oleh: Yuji Mikata, Aya Tsuruta, Hinata Koike, Sunao Shoji, Hideo Konno
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2024-01-01 |
Deskripsi
The development of fluorescent Cd<sup>2+</sup> sensors requires strict selectivity over Zn<sup>2+</sup> because of the high availability of Zn<sup>2+</sup> in the natural environment. In this paper, bisquinoline-based fluorescent sensors with a 2-aminoethanol backbone were investigated. The weak coordination ability of quinoline compared to well-studied pyridine is suitable for Cd<sup>2+</sup> selectivity rather than Zn<sup>2+</sup>. In the presence of 3 equiv. of metal ions, TriMeO-<i>N,O</i>-BQMAE (<i>N,O</i>-bis(5,6,7-trimethoxy-2-quinolylmethyl)-2-methylaminoethanol (<b>3</b>)), as well as its <i>N,N</i>-isomer TriMeO-<i>N,N</i>-BQMAE (<i>N,N</i>-bis(5,6,7-trimethoxy-2-quinolylmethyl)-2-methoxyethylamine (<b>6</b>)), exhibits Cd<sup>2+</sup>-selective fluorescence enhancement over Zn<sup>2+</sup> in DMF-HEPES buffer (1:1, 50 mM HEPES, 0.1 M KCl, pH = 7.5) (<i>I</i><sub>Zn</sub>/<i>I</i><sub>Cd</sub> = 26ā34%), which has similar selectivity in comparison to the corresponding ethylenediamine derivative TriMeOBQDMEN (<i>N,Nā</i>-bis(5,6,7-trimethoxy-2-quinolylmethyl)-<i>N,Nā</i>-dimethylethylenediamine) under the same experimental condition (<i>I</i><sub>Zn</sub>/<i>I</i><sub>Cd</sub> = 24%). The fluorescence mechanisms of <i>N,O</i>- and <i>N,N</i>-isomers of BQMAE are quite different, judging from the fluorescence lifetimes of their metal complexes. The Cd<sup>2+</sup> complex with TriMeO-<i>N,O</i>-BQMAE (<b>3</b>) exhibits a long fluorescence lifetime similar to that of TriMeOBQDMEN via intramolecular excimer emission, whereas the Cd<sup>2+</sup> complex with TriMeO-<i>N,N</i>-BQMAE (<b>6</b>) exhibits a short lifetime from monomer emission.