Photoswitches are compounds that change conformation in response to light, this is generally through the isomerization of bonds, with or without the breaking of bonds. Some photoswitches have been found to not only be light-sensitive but also redox- and heat-sensitive. Photoswitchable compounds have found many applications due to the changes in conformational, photochemical, and physical properties upon switching. One of the most commonly employed classes of photoswitches are the spiropyrans, as well as the related class of spirooxazines. The photoswitching capabilities of spiropyrans and spirooxazines are known and have been well studied. However, to date there has been no systematic study and comparison on how the electronic properties of substituents affect the photoswitching properties of these compounds. For this reason a matrix of spiropyrans and spirooxazines were synthesized in which electron donating and withdrawing groups were varied and incorporated on either side of the photoswitches. This enabled us to elucidate the electronic effects of photoswitching and directly compare spiropyrans to spirooxazines. Herein, the synthesis and photochemical properties of a range of spiropyran and spirooxazine photoswitches are described. The photoswitching properties of these compounds were also explored in the presence of various metals.

Systematic study and comparison of the photochemical properties of spiropyrans and spirooxazines

251st National Meeting (2016)

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