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 language | English |
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Pages (from-to) | 327-345 |
Number of pages | 19 |
Journal | Journal of Flow Chemistry |
Volume | 10 |
Issue number | 1 |
Early online date | 13 Feb 2020 |
DOIs | |
Publication status | Published - 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