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Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe 3+ , DFT Calculation and Their Antibacterial Activity
Author(s) -
Ooshall Farkhondeh,
Golbedaghi Reza,
Jamehbozorgi Saeed
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5430
Subject(s) - chemistry , schiff base , benzaldehyde , selectivity , fluorescence , metal ions in aqueous solution , condensation reaction , quenching (fluorescence) , metal , proton nmr , nuclear chemistry , inorganic chemistry , photochemistry , polymer chemistry , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
Two new Macroacyclic Schiff base chemosensors (L 1 and L 2 ) were synthesized by the one pot condensation reaction of 2‐[3‐(2‐formyl phenoxy)propoxy]benzaldehyde and aminophenol in a 1:2 molar ratio and were characterized by IR, NMR spectroscopy. Both Schiff bases displayed high selectivity and sensitivity towards Fe 3+ over other metal ions in H 2 O‐DMF solution (Ag + ,Cu 2+ , Ni 2+ , Zn 2+ , Mg +2 , Mn +2 , Pb +2 , Co +2 , Hg +2 , Cr +3 , Na + , Ba +2 and Cd 2+ ) due to their structure including oxygen donor atoms. The test results showed fluorescence quenching of the fluorophores when Fe 3+ was bound to the recognition units. From test results, a high selectivity for Fe 3+ were discovered in this type of sensors, especially, the probe based on 2‐aminophenol exhibited more significant quenching in fluorescence intensity compared with 4‐aminophenol‐based due to its rigidity structure. In addition, the structure of ligands and their antibacterial properties was investigated.