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Thermally stable photoswitches that are driven with low-energy light are rare, yet crucial for extending the applicability of photoresponsive molecules and materials towards,  e.g. , living systems. Combined  ortho -fluorination and -amination couples high visible light absorptivity of  o -aminoazobenzenes with the extraordinary bistability of  o -fluoroazobenzenes. Herein, we report a library of easily accessible  o -aminofluoroazobenzenes and establish structure–property relationships regarding spectral qualities, visible light isomerization efficiency and thermal stability of the  cis -isomer with respect to the degree of  o -substitution and choice of amino substituent. We rationalize the experimental results with quantum chemical calculations, revealing the nature of low-lying excited states and providing insight into thermal isomerization. The synthesized azobenzenes absorb at up to 600 nm and their thermal  cis -lifetimes range from milliseconds to months. The most unique example can be driven from  trans  to  cis  with any wavelength from UV up to 595 nm, while still exhibiting a thermal  cis -lifetime of 81 days. Graphical abstract

Towards low-energy-light-driven bistable photoswitches: ortho-fluoroaminoazobenzenes