Improving Continuous Flow Singlet Oxygen Photooxygenation Reactions with Functionalized Mesoporous Silica Nanoparticles

Continuous flow photochemistry relying on photosensitizers faces two main challenges: 1) Photodegradation (bleaching) and 2) the downstream removal of the photosensitizer. Rose bengal (RB) is a common photosensitizer utilized for photooxygenation reactions with singlet oxygen (1O2), but is notorious...

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Bibliographic Details
Published in:ChemPhotoChem 2018-10, Vol.2 (10), p.890-897
Main Authors: Mendoza, Carlos, Emmanuel, Noémie, Páez, Carlos A., Dreesen, Laurent, Monbaliu, Jean‐Christophe M., Heinrichs, Benoît
Format: Article
Language:English
Subjects:
continuous flow oxygenation
microreaction technology
photooxygenation
photosensitizer heterogenization
singlet oxygen
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Summary:Continuous flow photochemistry relying on photosensitizers faces two main challenges: 1) Photodegradation (bleaching) and 2) the downstream removal of the photosensitizer. Rose bengal (RB) is a common photosensitizer utilized for photooxygenation reactions with singlet oxygen (1O2), but is notoriously sensitive to photobleaching and difficult to remove from reactor effluents. The heterogenization of photosensitizers on mesoporous silica nanoparticles (MSNs) is arguably a viable option for such applications. Herein, we report on the use of RB covalently incorporated into MSNs (RB@MSNs) for photooxygenation reactions under continuous flow conditions. RB@MSNs enable the 1O2 photooxygenation of various organic substrates upon irradiation with 540 nm LEDs. A series of organic substrates were evaluated including methionine, α‐terpinene, 2‐furoic acid, triphenylphosphine, citronellol and cyclopentadiene. These results emphasize an improved resistance to photobleaching, and the possibility to use RB@MSNs as an easily recoverable catalyst, which could be removed from the reactor effluent either a) by centrifugation or b) by in‐line membrane filtration. Get in line! The immobilization of Rose Bengal (RB) onto mesoporous silica nanoparticles (MSNs) enabled the 1O2 photooxygenation of various organic substrates under microfluidic conditions upon irradiation with 540 nm LEDs. An improved resistance to photobleaching was obtained and the heterogenized photosensitizer could be easily recovered from the reactor effluent by in‐line membrane separation.
ISSN:2367-0932
2367-0932
DOI:10.1002/cptc.201800148