It is important, but challenging, to measure the (photo) induced switching of molecules in different chemical environments, from solution, to thin layers, to solid bulk crystals. We compare the cis-trans conformational switching of commercial azobenzene molecules in different liquid and solid environments: polar solutions, liquid polymers, 2D nanostructures and 3D crystals. We achieve this goal using complementary techniques: optical absorption spectroscopy, femtosecond transient absorbance spectroscopy, Kelvin probe force microscopy and reflectance spectroscopy, supported by density functional theory calculations. We could observe the same molecule showing fast switching in few picoseconds, when studied as isolated molecule in water, or slow switching in tens of minutes, when assembled in 3D crystals. Noteworthy, we could also observe switching for small ensembles of molecules (few attomoles …