Synthesis and application of monodisperse oligo(oxyethylene)-grafted polystyrene resins for solid-phase organic synthesis

ACS Comb Sci. 2014 Jul 14;16(7):367-74. doi: 10.1021/co500028h. Epub 2014 Jun 18.

Abstract

In a preliminary investigation by our group, we found that poly(styrene-oxyethylene) graft copolymers (PS-PEG), for example, TentaGel resins, are advantageous for gel-phase (13)C NMR spectroscopy. Because of the solution-like environment provided by the PS-PEG resins, good spectral quality of the attached moiety can be achieved, which is useful for nondestructive on-resin analysis. The general drawbacks of such resins are low loading capacities and the intense signal in the spectra resulting from the PEG linker (>50 units). Here, we describe the characterization of solvent-dependent swelling and reaction kinetics on a new type of resin for solid-phase organic synthesis (SPOS) that allows an accurate monitoring by gel-phase NMR without the above disadvantages. A series of polystyrene-oligo(oxyethylene) graft copolymers containing monodisperse PEG units (n = 2-12) was synthesized. A strong correlation between the linker (PEG) length and the line widths in the (13)C gel-phase spectra was observed, with a grafted PEG chain of 8 units giving similar results in terms of reactivity and gel-phase NMR monitoring to TentaGel resin. Multistep on-resin reaction sequences were performed to prove the applicability of the resins in solid-phase organic synthesis.

MeSH terms

  • Carbon Isotopes
  • Chemistry Techniques, Synthetic*
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Particle Size
  • Polyethylene Glycols / chemical synthesis*
  • Polyethylene Glycols / chemistry
  • Polystyrenes / chemical synthesis*
  • Polystyrenes / chemistry
  • Surface Properties

Substances

  • Carbon Isotopes
  • Polystyrenes
  • polyethylene glycol-polystyrene
  • Tentagel resin
  • Polyethylene Glycols