Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 31, Pages 6279-6286Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25852h
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Funding
- National Natural Science Foundation of China [20772013]
- Beijing National Natural Science Foundation [2122031]
- Beijing Municipal Commission of Education
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Three fluorescent probes CdABA', CdABA and ZnABA', which are structural isomers of ZnABA, have been designed with N,N-bis(2-pyridylmethyl) ethylenediamine (BPEA) as chelator and 2-aminobenzamide as fluorophore. These probes can be divided into two groups: CdABA, CdABA' for Cd2+ and ZnABA, ZnABA' for Zn2+. Although there is little difference in their chemical structures, the two groups of probes exhibit totally different fluorescence properties for preference of Zn2+ or Cd2+. In the group of Zn2+ probes, ZnABA/ZnABA' distinguish Zn2+ from Cd2+ with F-Zn(2+)-F-Cd(2+) = 1.87-2.00. Upon interchanging the BPEA and carbamoyl groups on the aromatic ring of the fluorophore, the structures of ZnABA/ZnABA' are converted into CdABA/CdABA'. Interestingly, the metal ions selectivity of CdABA/CdABA' was switched to discriminate Cd2+ from Zn2+ with F-Cd(2+)-F-Zn(2+) = 2.27-2.36, indicating that a small structural modification could lead to a remarkable change of the metal ion selectivity. 1H NMR titration and ESI mass experiments demonstrated that these fluorescent probers exhibited different coordination modes for Zn2+ and Cd2+. With CdABA' as an example, generally, upon addition of Cd2+, the fluorescence response possesses PET pathway to display no obvious shift of maximum lambda(em) in the absence or presence of Cd2+. However, an ICT pathway could be employed after adding Zn2+ into the CdABA' solution, resulting in a distinct red-shift of maximal lambda(em).
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