An o-hydroxyl aldehyde structure based naphthalimide derivative: Reversible photochromic properties and its application in ClO− detection in living cells.

A bifunctional organic compound 2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[ de ] isoquinoline-5-carbaldehyde (BHC) with photochromic properties in solid state and probe detection for ClO− in complete water solution was synthesized and fully characterized. A 'white–yellow–white' reversible photochromic behavior could be observed when alternating UV/vis light irradiation on the solid BHC powder. Good fatigue resistance and adjustable bleaching rate were shown when heating conditions changes. In addition, BHC displayed a high selectivity and low detection limit (1.16 × 10−8 M) for ClO−. The photoluminescent fluorescence "on-off" recognition result can be easily identified and BHC has been tested for safely imaging living cells and detecting hypochlorite anion in vitro and vivo. A better water solubility of BHC effectively reduces damage caused by organic solvent in cell imaging progress. Unlabelled Image • This is an interesting bifunctional material with reversible photochromic behavior and ClO− recognition effect. • BHC exhibits a rare naphthalimide-based ESIPT mechanism for photochromic properties and fatigue resistance. • This is a completely water soluble fluorescent probe. • BHC is capable of simultaneously detecting ClO− in aqueous solution and living cells • Probe BHC exhibits ideal properties including high sensitive, good selectivity and short response time. [ABSTRACT FROM AUTHOR]