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Updated: Sep 6, 2025

Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch
Published on: February 7, 2022
Regioisomerism in Symmetric Dimethyl Dialdehydes Dictates their Photochemical Reactivity
Florian Feist1, Leona L Rodrigues2,3, Sarah L Walden2,3
1Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
Abstract:
We herein report the first light-driven selective monoderivatization (desymmetrization) of two chemically equivalent carbonyl groups in a single chromophore. By comparing of four symmetric regioisomers, featuring two equivalent ortho-methylbenzaldehyde units, we identify dimethyltherephtalaldehydes (DMTAs) which can be activated in a dual wavelength-selective fashion. Under visible light and UV-light irradiation, DMTAs undergo two consecutive Diels-Alder reactions exhibiting near-quantitative endo-selectivity (>99%) and provide excellent yields (96-98%). The influence of the regioisomerism of the dialdehydes on their photochemical behavior is profound, evidenced by an in-depth investigation of their photochemical performance. We exemplify the capability of the photosystems via the synthesis of complex Diels-Alder adducts with various dienophiles, including alkynes.
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