The First Example of an Azaphenalene Profluorescent Nitroxide

Abstract

Abstract The synthesis of the first example of an azaphenalene‐based fused aromatic nitroxide TMAO, [1,1,3,3‐tetramethyl‐2,3‐dihydro‐2‐azaphenalen‐2‐yloxyl, ( 5 )], is described. This novel nitroxide possesses some of the structural rigidity of the isoindoline class of nitroxides, as well as some properties akin to TEMPO nitroxides. Additionally, the integral aromatic ring imparts fluorescence that is switched on by radical scavenging reactions of the nitroxide, which makes it a sensitive probe for polymer degradation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)