Improving Copper(II) Sensitivity by Combined use of AIEE Active and Inactive Schiff Bases

An aggregation-induced emission enhancement (AIEE) active Schiff base PNN was synthesized by condensing benzidine with 2-hydroxynaphthaldehyde. The green-fluorescent PNN (λ_em = 510 nm) in DMF turned to yellow-fluorescent PNN (λ_em = 557 nm) upon increasing the fractions of HEPES buffer (10 mM, pH 7.4) above 40%. The DLS study supports the self-aggregation of PNN that restricts the intramolecular rotation and activates the excited-state intramolecular proton transfer (ESIPT) process. The fluorescence emission of AIEE active PNN was quenched by Cu²⁺ with an estimated detection limit of 2.1 µM. Interestingly, the detection limit of PNN towards Cu²⁺ was improved in the presence of an AIEE inactive Schiff base PBPM obtained by reacting 1,4-diaminobenzene with pyridine-4-carbaldehyde. The mixed PNN-PBPM showed a detection limit of 0.49 µM. The practical utility of PNN-PBPM was validated by quantifying Cu²⁺ ions in real environmental water samples and green tea.