New Insights into Acylhydrazones E/Z Isomerization: An Experimental and Theoretical Approach

A family of acylhydrazones have been prepared and characterized with the aim of investigating their potential as information storage systems. Their well-established synthetic methodologies allowed for the preparation of seven chemically stable acylhydrazones in excellent yields that have been photophysically and photochemically characterized. In addition, DFT and TD-DFT calculations have been performed to gain more insights into the structural, energetic and photophysical properties of the E/Z isomers. Our results reveal that E/Z configurational isomerization upon irradiation is highly dependent on the stabilization of the E or Z isomers due to the formation of intramolecular H bonds and the electronic/steric effects intrinsically related to their structures. In addition, Raman spectroscopy is also used to confirm the molecular structural changes after the formation of hydrogen bonds in the isomers.

Automated summary

In this study, a family of acylhydrazones was synthesized and characterized for their potential as information storage systems. Their properties were investigated through photophysical and photochemical characterizations, as well as DFT and TD-DFT calculations. The results revealed that the configurational isomerization of the E/Z isomers upon irradiation is influenced by the stabilization of the isomers and the formation of intramolecular hydrogen bonds, along with the electronic/steric effects.