Abstract
The control of chemical functionalization with orthogonal light stimuli paves the way toward manipulating materials with unprecedented spatiotemporal resolution. To reach this goal, we herein introduce a photochemical reaction system that enables two-color control of covalent ligation via an oxo-Diels–Alder cycloaddition between two separate light-responsive molecular entities: a UV-activated photocaged diene based on ortho-quinodimethanes and a carbonyl dienophile appended to a diarylethene photoswitch, whose reactivity can be modulated upon illumination with UV and visible light.
Highlights
B y enabling chemical functionalization of molecules and materials with high efficiency and spatiotemporal control, photoinduced ligation reactions[1] are finding applications in a variety of fields ranging from polymer network formation[2] to surface patterning,3 3D printing,[4] and bioconjugation.[5]
We focus our attention on a photoligation process that has been seldomly explored for light-induced chemical functionalization: the oxo-Diels−Alder cycloaddition, a hetero-Diels−Alder reaction between dienes and carbonyl groups (Figure 1b).[10]
As for the electron-poor dienophile, we choose trifluoromethyl ketones,[15] which are tethered to a diarylethene photoswitch (DAE) to reversibly alter their reactivities upon photoisomerization (Figure 1c)
Summary
N. The Power of Light in Polymer Science: Photochemical Processes to Manipulate Polymer Formation, Structure, and Properties. V. Attach, Remove, or Replace: Reversible Surface Functionalization Using Thiol−Quinone Methide Photoclick Chemistry.
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