Indolino-oxazolidine derivatives are a new and pretty confidential family of multimodal molecular switch. Indeed, acid, electrochemical potential, and UV light irradiation can be used to convert these compounds form their colorless closed form to a colorful open form. In this publication, we have investigated the influence of the extension of the p-conjugated system beared by the indolino moiety on their halo-, electro- and photochromic properties. In this context, we have demonstrated that only their photochemical properties are strongly affected by this structural modification. Moreover, quantum chemistry calculations have allowed to rationalize our experimental observations and, noticeably, to evidence an oxidative quenching process in presence of chlorobenzene, which enhances their reactivity.