Continuous-flow synthesis and application of polymer-supported BODIPY Photosensitisers for the generation of singlet oxygen; process optimised by in-line NMR spectroscopy

Christopher G. Thomson, Callum M. S. Jones, Georgina Rosair, David Ellis, Jose Marques-Hueso, Ai-Lan Lee, Filipe Vilela

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Abstract

Commercial polystyrene Merrifield-type resins have been post-synthetically functionalised with BODIPY photosensitisers via a novel aryl ester linking strategy in continuous-flow. A unique synthetic advantage of post-synthetically modifying heterogeneous materials in flow was identified. The homogeneous analogues of the polymer-supported BODIPYs were synthesised and used as reference to assess photophysical properties altered by the polymer-support and linker. The homogeneous and polymer-supported BODIPYs were applied in visible-light photosensitisation of singlet oxygen for the conversion of α-terpinene to ascaridole. Materials produced in flow were superior to batch in terms of functional loading and photosensitisation efficiency. Flow photochemical reactions generally outperformed batch by a factor of 4 with respect to rate of reaction. The polymer-supported BODIPY resins could be irradiated for 96 h without loss of photosensitising ability. Additional material synthetic modification and conditions optimisation using an in-line NMR spectrometer resulted in a 24-fold rate enhancement from the initial material and conditions. [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)327-345
Number of pages19
JournalJournal of Flow Chemistry
Volume10
Issue number1
Early online date13 Feb 2020
DOIs
Publication statusPublished - Mar 2020

Keywords

  • BODIPY
  • In-line NMR reaction monitoring
  • Merrifield resins
  • Organic photosensitisers
  • Singlet oxygen
  • Visible light

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Fluid Flow and Transfer Processes
  • Organic Chemistry

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