Photoinduced Proton-Transfer Polymerization: A Practical Synthetic Tool for Soft Lithography Applications

Hyunki Yeo, Anzar Khan

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Proton-transfer photopolymerization through the thiol-epoxy "click" reaction is shown to be a versatile new method for the fabrication of micro- A nd nanosized polymeric patterns. In this approach, complexation of a guanidine base, diazabicycloundecene (DBU), with benzoylphenylpropionic acid (ketoprofen) generates a photolabile salt. Under illumination at a wavelength of 365 nm, the salt undergoes a photodecarboxylation reaction to release DBU as a base. The base-catalyzed ring opening reaction then creates cross-linked poly(β-hydroxyl thio-ether) patterns. The surface chemistry of these patterns can be altered through alkylation of the thio-ether linkages. For example, a reaction with bromoacetic acid produces a hitherto unknown sulfonium/carboxylate-based zwitterionic motif that endows antibiofouling capacity to the micropatterns.

Original languageEnglish
Pages (from-to)3479-3488
Number of pages10
JournalJournal of the American Chemical Society
Volume142
Issue number7
DOIs
Publication statusPublished - 2020 Feb 19

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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