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Photoreactive Polymer Brushes for High-Density Patterned Surface Derivatization Using a Diels–Alder Photoclick Reaction

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journal contribution
posted on 22.02.2016 by Selvanathan Arumugam, Sara V. Orski, Jason Locklin, Vladimir V. Popik
Reactive polymer brushes grown on silicon oxide surfaces were derivatized with photoreactive 3-(hydroxymethyl)­naphthalene-2-ol (NQMP) moieties. Upon 300 or 350 nm irradiation, NQMP efficiently produces o-naphthoquinone methide (oNQM), which in turn undergoes very rapid Diels–Alder addition to vinyl ether groups attached to a substrate, resulting in the covalent immobilization of the latter. Any unreacted oNQM groups rapidly add water to regenerate NQMP. High-resolution surface patterning is achieved by irradiating NQMP-derivatized surfaces using photolithographic methods. The Diels–Alder photoclick reaction is orthogonal to azide–alkyne click chemistry, enabling sequential photoclick/azide-click derivatizations to generate complex surface functionalities.