Polylutidines: Multifunctional Surfaces through Vapor-Based Polymerization of Substituted Pyridinophanes

Florence Bally-Le Gall, Christoph Hussal, Joshua Kramer, Kenneth Cheng, Ramya Kumar, Thomas Eyster, Amy Baek, Vanessa Trouillet, Martin Nieger, Stefan Bräse, Joerg Lahann

Research output: Contribution to journalArticlepeer-review

Abstract

We report a new class of functionalized polylutidine polymers that are prepared by chemical vapor deposition polymerization of substituted [2](1,4)benzeno[2](2,5)pyridinophanes. To prepare sufficient amounts of monomer for CVD polymerization, a new synthesis route for ethynylpyridinophane has been developed in three steps with an overall yield of 59 %. Subsequent CVD polymerization yielded well-defined films of poly(2,5-lutidinylene-co-p-xylylene) and poly(4-ethynyl-2,5-lutidinylene-co-p-xylylene). All polymers were characterized by infrared reflection–absorption spectroscopy, ellipsometry, contact angle studies, and X-ray photoelectron spectroscopy. Moreover, ζ-potential measurements revealed that polylutidine films have higher isoelectric points than the corresponding poly-xylylene surfaces owing to the nitrogen atoms in the polymer backbone. The availability of reactive alkyne groups on the surface of poly(4-ethynyl-2,5-lutidinylene-co-p-xylylene) coatings was confirmed by spatially controlled surface modification by means of Huisgen 1,3-dipolar cycloaddition. Compared to the more hydrophobic poly-p-xylylyenes, the presence of the heteroatom in the polymer backbone of polylutidine polymers resulted in surfaces that supported an increased adhesion of primary human umbilical vein endothelial cells (HUVECs). Vapor-based polylutidine coatings are a new class of polymers that feature increased hydrophilicity and increased cell adhesion without limiting the flexibility in selecting appropriate functional side groups.

Original languageEnglish (US)
Pages (from-to)13342-11335
Number of pages2008
JournalChemistry - A European Journal
Volume23
Issue number54
DOIs
StatePublished - Sep 27 2017
Externally publishedYes

Keywords

  • alkynes
  • chemical vapor deposition
  • click chemistry
  • pyridinophanes
  • reactive coatings

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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