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- Title
Synthesis of novel azo linkage-based Schiff bases including anthranilic acid and hexanoic acid moieties: investigation of azo-hydrazone and phenol-keto tautomerism, solvatochromism, and ionochromism.
- Authors
ÖZDEMİR, Özlem
- Abstract
Two new azo-Schiff base receptors (L1 and L2) containing azo and azomethine groups with a conjugated group (benzyl ring of anthranilic acid, in L1) and electron-donating group (alkyl chain of hexanoic acid, in L2) were synthesized and characterized. Azo-hydrazone/phenol-keto tautomerism and solvatochromism were investigated. Studying their sensing ability towards cations (Co2+ , Cu2+ , Zn2+ , Ni2+ , Pb2+ , Cd2+ , Mn2+ , Fe3+ , Cr3+ , and Al3+) , high sensitivity and selectivity were recorded for Fe3+ by naked eye and UV-Vis spectra in DMF-aqueous HEPES buffer (v:v, 1:1, pH 6.8). The color of L1 and L2 solutions instantly changed from yellow to deep orange and pale orange. L2 sensed Cu2+ and Al3+ ions selectively by UV-Vis spectra. The interactions of receptors with F- , Cl- , CH3 COO- , C2 O2-4 , H2 PO- 4 , and OH- anions were also investigated in DMF-HEPES 1:1 and 4:1 solvent mixtures. L1 sensitively responded to anions according the order of OH- >C2 O2- 4 >F- in the 1:1 mixture and OH- >F- >CH3 COO- >C2 O2-4 in the 4:1 mixture in UV-Vis spectra with color changing from pale yellow to dark yellow. However, L2 showed weak spectral changes in the UV-Vis spectra, so its sensitivity was poorer than L1 , attributed to the effect of alkyl chains.
- Subjects
AZO compound synthesis; SCHIFF bases; AMINOBENZOIC acids; MOIETIES (Chemistry); HYDRAZONES; PHENOLS; SOLVATOCHROMISM; TAUTOMERISM
- Publication
Turkish Journal of Chemistry, 2019, Vol 43, Issue 1, p266
- ISSN
1300-0527
- Publication type
Article
- DOI
10.3906/kim-1807-24