A fluorescent and colorimetric chemosensor for nitric oxide based on 1,8-naphthalimide

A fluorescent chemosensor N-n-butyl-3,4-diamino-1,8-naphthalimide (DAN) for detecting NO was developed on the basis of 1,8-naphthalimide with a similar structure of o-phenylenediamine as a NO reaction site. Due to the interaction between the photoinduced electron transfer (PET) and the intramolecular charge transfer (ICT), the chemosensor exhibits a remarkable enhancement in the emission intensity that is ca. 160-fold increase and a blue shift in the emission wavelength after the addition of NO. Meanwhile, it displays a colorimetric response accompanied with a color change from yellow to colorless. The chemosensor DAN shows a high selectivity for NO in the presence of various reactive nitrogen species (RNS) and reactive oxygen species (ROS). Furthermore, DAN can be used for bioimaging of NO in living cells.

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► A fluorescent chemosensor for detecting nitric oxide (NO) was synthesized.
► The chemosensor was extremely sensitive to NO with about 160-fold fluorescence enhancement.
► It can rapidly and selectively detect NO in a colorometric way.
► The molecule can penetrate cell membrane easily and make fast fluorescence bioimaging.