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Superoxide anion (O 2 •−), the first generated reactive oxygen species (ROS), is a critical player in cellular signaling network and redox homeostasis. Imaging of O 2 •−, particularly in vivo , is of concern for further understanding its roles in pathophysiological and pharmacological events. Herein, we designed a novel probe, (E)-4-(5-(2-(benzo[ d ]thiazol-2-yl)-2-cyanovinyl)furan-2-yl)phenyl trifluoromethane-sulfonate (BFTF), by modifying hydroxyphenyl benzothiazole (a widely used dye scaffold) which includes insertion of both an acrylonitrile unit and a furan ring to extend the total π-conjugation system and to enhance push-pull intramolecular charge transfer process, and utilization of trifluoromethanesulfonate as the response unit. Toward O 2 •−, the probe features near-infrared fluorescent emission (685 nm), large Stokes shift (135 nm), and deep tissue penetration (300 μm). With its help, we successfully mapped preferential generation of O 2 •− in HepG2 cells over L02 cells, as well as in A549 over BEAS-2B cells by β-lapachone (an anticancer agent that generates O 2 •−), and more importantly, visualized overproduction of O 2 •− in living mice with liver injury induced by acetaminophen (a well-known analgesic and antipyretic drug). [Display omitted] • Designing BFTF as a near-infrared O 2 •− probe by modifying benzothiazole. • Identifying that β-lapachone is a prooxidative anticancer agent via O 2 •− generation. • Applying for intravital imaging of O 2 •− overproduction induced by acetaminophen. [ABSTRACT FROM AUTHOR]