A Naphthalimide-Based Cd(2+) Fluorescent Probe with Carbamoylmethyl Groups Working as Chelators and PET-Promoters...

We have developed a novel naphthalimide-based Cd(2+) fluorescent probe (1), featuring almost no background response, high sensitivity and selectivity toward Cd(2+) through its high association constant [K=(2.10±0.423)×10(6) ], and a practical working pH range. Membrane-permeability was conferred on 1 by replacing the imide and amide substituents with n-butyl groups, and hence the derivative (4) has found practical utility on fluorescent imaging of Cd(2+) in HeLa cells. Comparison of fluorescent properties between various compounds derived from 1 has demonstrated that the carbamoylmethyl groups in 1 function not only as Cd(2+) chelators but also as promoters for photoinduced electron transfer (PET) by lowering the basicity of the two tertiary amino groups. As a result, 1 and 4 exhibited highly practical performance as Cd(2+) probes under neutral conditions.