Synthesis, characterization and Cu2+ triggered selective fluorescence quenching of Bis-calix[4]arene tetra-triazole macrocycle

[Display omitted] •The 9 was characterized by Mass, NMR spectroscopy and X-ray crystallography.•The 9 lost fluorescence after mixing with Cu2+..•The lower limit of detection for Cu2+ by 9 was found to be 40nM.•The chemosensor 9 recognized Cu2+ in living cells selectively A novel fluorescent bis-cali...

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Bibliographic Details
Published in:Journal of hazardous materials 2016-05, Vol.309, p.97-106
Main Authors: Khan, Burhan, Shah, Muhammad Raza, Ahmed, Dania, Rabnawaz, Muhammad, Anis, Itrat, Afridi, Saifullah, Makhmoor, Talat, Tahir, Muhammad Nawaz
Format: Article
Language:English
Subjects:
Atomic force microscopy
Bis-calixarene
Cations
Copper
Drinking water
Fluorescence
Macrocycle
Macrocyclic compounds
Mercury (metal)
Nuclear magnetic resonance
Pakistan
Quenching
Supramolecular
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Summary:[Display omitted] •The 9 was characterized by Mass, NMR spectroscopy and X-ray crystallography.•The 9 lost fluorescence after mixing with Cu2+..•The lower limit of detection for Cu2+ by 9 was found to be 40nM.•The chemosensor 9 recognized Cu2+ in living cells selectively A novel fluorescent bis-calix[4]arene macrocycle 9 incorporating metal-binding pockets was successfully prepared. The structure of macrocycle 9 and its precursors were characterized via EI-MS, MALDI-TOF-MS, ESI-MS, 1H NMR, 13CNMR, 2D NMR, and X-ray crystallography. The macrocycle 9 displayed selective fluorescence quenching after interacting with Cu2+ in the presence competing metal cations including Mg2+, Ca2+, Ba2+, Ag+, Zn2+, Ti4+,Cd2+, Hg2+, Pb2+, In3+, La3+, Cr3+, Ni2+, Sb3+, V5+, Fe3+, Co2+, Sn2+, Sn2+, and Tl+. The Cu2+ limit of detection was found to be 40nM much lower than its threshold level (∼20μM) in drinking water permitted by the U.S Environmental Protection Agency (EPA). Furthermore, drinking water samples from Karachi University (Pakistan) spiked with Cu2+ were analysed with the sensing system and the results showed an excellent agreement with the fluorescence quenching phenomenon of macrocycle 9 examined in deionized water. Importantly, the chemosensor 9 could be used to detect Cu2+ in living cells
ISSN:0304-3894
1873-3336
DOI:10.1016/j.jhazmat.2016.01.074