It is well known that excessive levels of sulfur dioxide and its derivatives are connected to diverse diseases. Therefore, developing highly sensitive probes to detect and monitor sulfite in living cells is important for the diagnosis of disease and the study of biochemical processes in vivo. In this report, two zero cross-talk ratiometric fluorescent probes were synthesized (CA-ID-MC and CA-BI-MC), which were derived from carbazole-indolenine π-conjugated system for effective detection of sulfite in living cells. Observably, CA-BI-MC exhibited the largest emission shift of 157 nm from 617 to 460 nm with the addition of various concentrations of sulfite, which is beneficial for high-resolution imaging of the sulfite. CA-BI-MC also exhibits high sensitivity and low cytotoxicity. More importantly, this probe successfully located mitochondria and sensed the sulfite in HeLa cells caused by exogenous stimulation.
Taking advantages of both the well-known α,β-unsaturated structure and the special nucleophilicity of organic amines toward its acceptor moieties, intramolecular charge transfer as a signaling mechanism is used to design and synthesize a new ratiometric chromophoric fluorescent probe (BI-CA-ID) with large emission shifts toward organic amines. This probe is employed for the detection of organic amines with high selectivity and sensitivity and a “naked-eye” color change (from red to colorless). Ultraviolet–visible and fluorescence spectrometric measurements are used to determine detection limits as low as 0.024 and 0.43 μM. Furthermore, nucleophilic addition of the amine on the α,β-unsaturated of BI-CA-ID indicated that the sensing mechanism occurs via interruption of the π-conjugation.
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