Di(acenaphtho)BODIPYs as deep red fluorescence probes for reactive oxygen species

Abstract

Some molecular probes that can detect reactive oxygen species (ROS) with deep-red fluorescence (FL) were designed and synthesized through modification of di(acenaphtho)BODIPY (DAB), which has a sharp absorption band around 680 nm. In order to detect ROS, anthracene or maleimide moiety was substituted at α- or meso-position of DAB, which would work as an FL switch. The obtained DAB having an anthracene moiety at the α-position showed suppressed FL and potential usefulness as a probe for detecting 1O2 and the 2-cyano-2-propyl radical (•CP) in acetonitrile. On the other hand, although DAB having an N-phenylmaleimide moiety at the meso-position showed suppressed FL, it could detect neither the hydroxyl radical nor •CP. DAB having a hydroxylamine moiety, which was accidently obtained as an intermediate in synthesis, worked as a •CP probe in ethanol and in acetonitrile. These DAB probes are promising tools for studying objects of interest related to ROS such as behaviors caused by oxidative stresses, antioxidation processes in living bodies, medicinal substances, food factors, and so on.