Photocages (PPGs) allow the temporally and spatially selective release of biologically active agents, exploiting a light stimulus for the cleavage of a covalent bond between the protecting group and the attached substrate [1]. Beyond the first described neuroscientific applications, photocages can serve as a drug-delivery system for different small molecule drugs [2]. We aimed to prepare and characterize novel 8-aminoquinoline derivatives [3], choosing the 8- dimethylaminoquinoline photocage as our starting point. We wished to implement a simple and robust synthetic pathway and study the effect of modifications in position 8 on the photophysical and photochemical properties. To better understand the structure-property relationships and to guide future PPG design, we set out to study the uncaging process by computational chemistry.