Abstract
Phenazines bearing electron-donor and electron-acceptor groups with high pH-sensing behavior were synthesized in moderate to good yields. Theoretical calculations on the frontier molecular orbitals and experimental oxidation potential measurements under variable pH values provide evidence for extensive internal charge transfer at high pH value. The well-known strong affinity of the catecholate moiety present in our phenazines is utilized for spectrophotometric detection of Fe3+ ion. Fluorescence-quenching behavior of the prepared phenazines is utilized for detection and distinction of electron-rich and electron-poor aromatics.
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