Predicting wavelength-dependent photochemical reactivity and selectivity

Jan P. Menzel, Benjamin B. Noble, James P. Blinco () and Christopher Barner-Kowollik ()
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Jan P. Menzel: Queensland University of Technology (QUT)
Benjamin B. Noble: RMIT University
James P. Blinco: Queensland University of Technology (QUT)
Christopher Barner-Kowollik: Queensland University of Technology (QUT)

Nature Communications, 2021, vol. 12, issue 1, 1-12

Abstract: Abstract Predicting the conversion and selectivity of a photochemical experiment is a conceptually different challenge compared to thermally induced reactivity. Photochemical transformations do not currently have the same level of generalized analytical treatment due to the nature of light interaction with a photoreactive substrate. Herein, we bridge this critical gap by introducing a framework for the quantitative prediction of the time-dependent progress of photoreactions via common LEDs. A wavelength and concentration dependent reaction quantum yield map of a model photoligation, i.e., the reaction of thioether o-methylbenzaldehydes via o-quinodimethanes with N-ethylmaleimide, is initially determined with a tunable laser system. Combined with experimental parameters, the data are employed to predict LED-light induced conversion through a wavelength-resolved numerical simulation. The model is validated with experiments at varied wavelengths. Importantly, a second algorithm allows the assessment of competing photoreactions and enables the facile design of λ-orthogonal ligation systems based on substituted o-methylbenzaldehydes.

Date: 2021
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DOI: 10.1038/s41467-021-21797-x

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