Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response

Abstract

Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.