Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
Volume 385, Issue -, Pages -Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2019.112038
Keywords
Furan; Hydrazone; Fluoride; Cyanide; Thiophene; Chemosensor; Schiff base
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Funding
- Thailand Research Fund [RSA6280049, DPG6080001, IRG5980007]
- Center of Excellence for Innovation in Chemistry (PERCH-CIC)
- Ministry of Higher Education, Science, Research and innovation
- Mahidol University
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Four dual optical signalings of fluorescent hydrazone Schiff bases were synthesized from 1,8-naphthalimide hydrazide and substituted furan and thiophene rings, employing ethanol as green solvent. All synthesized molecules can detect F- and CN- with fast response with naked eye color change and quenching of fluorescence. Most common competitive anions have paltry interferences during the optical sensing of F-, while only nitro and methyl furan substituted provided good selectivity to CN- in THF. Substituents on heterocyclic directly affect fluoride capturing sensitivity, namely, electron donating group provides more sensitivity than with electron withdrawing groups. H-1 NMR confirms the H-bonding between sensor molecule and F-/CN-. The detection limits of the four-sensor molecules were found below 0.3 ppm for F- and CN- detection. The magnitude of fluorescence quenching was estimated through Stern-Volmer plots. Test strips experimentation revealed the on-site solid-state detection efficacy of the sensors. Addition of Cu(II) ions to nitro and methyl furan substituted, resulted in selective discrimination between F- and CN- in THF. Computational studies prove the agreement of reactivity for four optical molecules interaction with F- and show that substituent at furan/thiophene does not affect the sensitivity, this is contrary to traditional school of thoughts.
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