The structure characteristics of photoproducts of indolinospirooxazines

Photochromic reactions of four indolinospirooxazine derivatives have been studied using nanosecond laser flash photolysis techniques. Photolysis of the four compounds in acetonitrile and in cyclohexane all leads to the formation of the short-lived CT intermediates as the predominant photoproducts. In certain circumstances few photomerocyanines (PMC) can be observed. From the absorption bands and the lifetimes of CT intermediates, it has been speculated that the substituents at the nitrogen atom of the indole ring influence the structural characteristics of CT intermediates mainly through steric hindrance effects, whereas the substituents at the 5 position of the indoline ring influence mainly through electron effects. A potential energy surface model is established to explain the results.