Indolino-oxazolidine Acido and Photochromic System investigated by NMR and DFT Calculations

Three addressable indolino-oxazolidine units connected through an isomerizable double bond to a substituted thiophene represent a smart example of multi-addressable system whose reversible responses could be selectively activated on demand. Experimental and theoretical approaches to push forward the understanding of the system mechanism, and set pathways to design optimized compounds for suitable application are here presented. NMR and UV-Visible spectroscopies are used for structural and kinetic studies, while Density Functional Theory (DFT) calculations pave the way to highlight energetic and electronic processes that are involved. Substitution and solvent effects towards the reactivity of the compounds are experimentally studied, and combined with theoretical calculations. The most efficient and selective stimuli to travel between the four possible states resulting from ring-opening of BOX and trans-cis isomerization of the ethylenic junction are elucidated.