| Autor: |
Wataru Inoue, Makoto Miyasaka, Kotoha Kazama, Masaki Tsuboi |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
Journal of Photochemistry and Photobiology A: Chemistry. 425:113688 |
| ISSN: |
1010-6030 |
| DOI: |
10.1016/j.jphotochem.2021.113688 |
| Popis: |
A novel Schiff base chiral macrocycle (C-1) was synthesized by the self-condensation of the dialdehyde of the chiral dinaphtho[2,1-d:1',2'-f] [1] , [3] dioxepine derivative and (1S,2S)-(+)-cyclohexanediamine under template-free conditions in moderate yield. The UV-vis and fluorescence spectral studies indicated that C-1 form the complex with metal ions into a 1:2 ratio based on Job’s plots. The obtained polyimine macrocycle represented an extraordinary fluorescence enhancement of ca 160 times in the presence of Zn2+ due to the PET and CHEF mechanism. The association constant for the C-1−Zn2+ complex was found to be 1.1 × 1010 M–2 and the “turn-on” detection limit of C-1 for the Zn2+ ion was as low as 1.91 nM. The chiral macrocycle C-1 enantioselectively recognized the L-phenyl glycinol than the D-isomer and exhibited a fluorescence enhancement. Furthermore, the in-situ generated Zn2+ containing the C-1−Zn2+ complex recognized the D- phenylalanine rather than the L-isomer and exhibited a “turn-off” response. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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