Backbone-Degradable Polymers Prepared by Chemical Vapor Deposition

Angew Chem Int Ed Engl. 2017 Jan 2;56(1):203-207. doi: 10.1002/anie.201609307. Epub 2016 Nov 30.

Abstract

Polymers prepared by chemical vapor deposition (CVD) polymerization have found broad acceptance in research and industrial applications. However, their intrinsic lack of degradability has limited wider applicability in many areas, such as biomedical devices or regenerative medicine. Herein, we demonstrate, for the first time, a backbone-degradable polymer directly synthesized via CVD. The CVD co-polymerization of [2.2]para-cyclophanes with cyclic ketene acetals, specifically 5,6-benzo-2-methylene-1,3-dioxepane (BMDO), results in well-defined, hydrolytically degradable polymers, as confirmed by FTIR spectroscopy and ellipsometry. The degradation kinetics are dependent on the ratio of ketene acetals to [2.2]para-cyclophanes as well as the hydrophobicity of the films. These coatings address an unmet need in the biomedical polymer field, as they provide access to a wide range of reactive polymer coatings that combine interfacial multifunctionality with degradability.

Keywords: CVD polymerization; cyclic ketene acetals; free-radical ring-opening polymerization; functional polymers; hydrolytic degradation.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetals / chemical synthesis
  • Acetals / chemistry*
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry
  • Chemistry Techniques, Synthetic / methods*
  • Cyclization
  • Ethers, Cyclic / chemical synthesis
  • Ethers, Cyclic / chemistry*
  • Ethylenes / chemical synthesis
  • Ethylenes / chemistry*
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Oxepins / chemical synthesis
  • Oxepins / chemistry
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Polymerization*
  • Polymers / chemical synthesis
  • Polymers / chemistry*
  • Volatilization

Substances

  • 2-methylene-1,3-dioxepane
  • Acetals
  • Biocompatible Materials
  • Ethers, Cyclic
  • Ethylenes
  • Ketones
  • Oxepins
  • Piperidines
  • Polymers
  • cyclophane 2
  • ketene