A robust method for functionalizing poly(cyclic olefin) surfaces comprised of Zeonor 1060R was developed. These surfaces were first oxidized using two separate methods, ozonolysis and oxygen plasma treatment, to increase their hydrophilic properties and produce carboxylic acids on the surface. The resulting acids enabled direct amide coupling with various amines containing azide or alkyne moieties onto the surface. These modified surfaces were further functionalized via copper-catalyzed azide–alkyne cycloadditions (CuAAC) on the surface and the method was optimized for this material. Surface modifications were characterized by water contact angle measurements, fluorescence microscopy, atomic force microscopy, and X-ray photoelectron spectroscopy. Our data demonstrates a robust method for generating “clickable” Zeonor 1060R surfaces as demonstrated through attachment and subsequent detection of a triazole-linked fluorophore. The method developed enables the systematic modification of any poly(cyclic olefin) surface for functionalization using the click reaction.
A series of six-membered rings bearing cis oriented vicinal carboxylate and sulfinate esters were treated with Grignard reagents with the intention of transforming them to -carboalkoxy substituted sulfoxides. The expected outcome did not transpire and instead the substrates demonstrated the capacity to accept 3 equiv. of organometallic agent in an uncontrollable manner. As such, the substrates possessing eclipsing carboxylate and sulfinate esters accepted two organic ligands at the carboxylate functionality and one at the sulfinyl group. When isomer mixtures of sterically encumbered sulfinate esters were reacted, a single sulfoxide stereochemistry resulted. A mechanism involving the intermediacy of a sulfurane is proposed to account for the experimental observations. Résumé : Une série de cycles à six membres portant des esters carboxyliques et sulfiniques vicinaux ont été traités avec des réactifs de Grignard dans le but de les transformer en -carboalkoxy sulfoxydes substitués. Le résultat espéré n'a pas été obtenu et, au lieu de cela, les substrats ont montré une capacité à accepter trois équivalents d'agent organométallique de manière incontrôlable. En tant que tels, les substrats portant des esters carboxyliques et sulfiniques en position éclipsante ont accepté deux ligands organiques au niveau de la fonction carboxylate et un au niveau du groupe sulfinyl. La réaction de mélanges isomériques d'esters sulfiniques stériquement encombrés a débouché sur une seule stéréochimie du sulfoxyde. Un mécanisme impliquant l'intermédiaire d'un sulfurane est proposé, qui permet d'expliquer les observations expérimentales. [Traduit par la Rédaction]Mots-clés : réactif de Grignard, ester sulfinique, sulfoxyde, réaction d'addition, sulfurane.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.