Mapping Dithiobenzoate-Mediated RAFT Polymerization Products via Online Microreactor/Mass Spectrometry Monitoring
2-cyano-2-propyl dithiobenzoates (CPDB)-mediated reversible addition-fragmentation chain transfer (RAFT) polymerization was monitored by online flow microreactor/mass spectrometry. This enabled the reactions to be followed in a time-resolved manner, closely resolving product patterns in the reaction...
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| Vydáno v: | Polymers Ročník 10; číslo 11; s. 1228 |
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06.11.2018
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| Abstract | 2-cyano-2-propyl dithiobenzoates (CPDB)-mediated reversible addition-fragmentation chain transfer (RAFT) polymerization was monitored by online flow microreactor/mass spectrometry. This enabled the reactions to be followed in a time-resolved manner, closely resolving product patterns in the reaction mixtures at any point in time. RAFT polymerization was investigated for low RAFT to monomer ratios, enabling the monitoring of the early stages of a typical RAFT polymerization. The expected transition from pre- to the RAFT main equilibrium is observed. However, very high abundancies for cross-termination products were also identified, both in the pre- and main equilibrium stage. This is a somewhat surprising result as such products have always been expected, but to date have not been observed in the majority of studies. Product isolation and NMR analysis revealed that cross-termination occurs in the para position of the benzoate ring and becomes fully irreversible via re-aromatization of the ring in a H-shift reaction. The present data suggest a pronounced chain-length dependence of the cross-termination reaction, which would explain why the products are seen here, but not in other studies. |
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| AbstractList | 2-cyano-2-propyl dithiobenzoates (CPDB)-mediated reversible addition-fragmentation chain transfer (RAFT) polymerization was monitored by online flow microreactor/mass spectrometry. This enabled the reactions to be followed in a time-resolved manner, closely resolving product patterns in the reaction mixtures at any point in time. RAFT polymerization was investigated for low RAFT to monomer ratios, enabling the monitoring of the early stages of a typical RAFT polymerization. The expected transition from pre- to the RAFT main equilibrium is observed. However, very high abundancies for cross-termination products were also identified, both in the pre- and main equilibrium stage. This is a somewhat surprising result as such products have always been expected, but to date have not been observed in the majority of studies. Product isolation and NMR analysis revealed that cross-termination occurs in the para position of the benzoate ring and becomes fully irreversible via re-aromatization of the ring in a H-shift reaction. The present data suggest a pronounced chain-length dependence of the cross-termination reaction, which would explain why the products are seen here, but not in other studies. 2-cyano-2-propyl dithiobenzoates (CPDB)-mediated reversible addition-fragmentation chain transfer (RAFT) polymerization was monitored by online flow microreactor/mass spectrometry. This enabled the reactions to be followed in a time-resolved manner, closely resolving product patterns in the reaction mixtures at any point in time. RAFT polymerization was investigated for low RAFT to monomer ratios, enabling the monitoring of the early stages of a typical RAFT polymerization. The expected transition from pre- to the RAFT main equilibrium is observed. However, very high abundancies for cross-termination products were also identified, both in the pre- and main equilibrium stage. This is a somewhat surprising result as such products have always been expected, but to date have not been observed in the majority of studies. Product isolation and NMR analysis revealed that cross-termination occurs in the para position of the benzoate ring and becomes fully irreversible via re-aromatization of the ring in a H-shift reaction. The present data suggest a pronounced chain-length dependence of the cross-termination reaction, which would explain why the products are seen here, but not in other studies.2-cyano-2-propyl dithiobenzoates (CPDB)-mediated reversible addition-fragmentation chain transfer (RAFT) polymerization was monitored by online flow microreactor/mass spectrometry. This enabled the reactions to be followed in a time-resolved manner, closely resolving product patterns in the reaction mixtures at any point in time. RAFT polymerization was investigated for low RAFT to monomer ratios, enabling the monitoring of the early stages of a typical RAFT polymerization. The expected transition from pre- to the RAFT main equilibrium is observed. However, very high abundancies for cross-termination products were also identified, both in the pre- and main equilibrium stage. This is a somewhat surprising result as such products have always been expected, but to date have not been observed in the majority of studies. Product isolation and NMR analysis revealed that cross-termination occurs in the para position of the benzoate ring and becomes fully irreversible via re-aromatization of the ring in a H-shift reaction. The present data suggest a pronounced chain-length dependence of the cross-termination reaction, which would explain why the products are seen here, but not in other studies. |
| Author | Junkers, Tanja Haven, Joris J. |
| AuthorAffiliation | 1 Polymer Reaction Design Group, School of Chemistry, Monash University, 19 Rainforest Walk, Clayton, VIC 3800, Australia; joris.haven@monash.edu 2 Institute for Materials Research, Hasselt University, Martelarenlaan 42, 3500 Hasselt, Belgium |
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| Cites_doi | 10.1002/mats.201600048 10.1002/marc.200900907 10.1002/pola.23385 10.1002/masy.200750217 10.1039/C4SC02908A 10.3390/polym10030318 10.1021/cr990119u 10.1002/pola.24857 10.1002/1521-3919(20021101)11:8<823::AID-MATS823>3.0.CO;2-R 10.1021/ma990316v 10.1021/cr940534g 10.1002/1097-0126(200009)49:9<993::AID-PI506>3.0.CO;2-6 10.1002/macp.201200668 10.1039/C7PY00360A 10.1002/marc.201400518 10.1002/ejoc.201700851 10.1021/ma001484m 10.1039/c0py00245c 10.1002/macp.201700381 10.1002/mren.201700016 10.1039/C4CC10426A 10.1016/j.ces.2017.11.043 10.1021/ma0628634 10.1021/ma800388c 10.1021/ma9804951 10.1002/marc.200600317 10.1002/pola.21589 10.1002/marc.201500357 10.1002/pola.10854 10.1002/marc.200500832 |
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| SubjectTerms | Addition polymerization Benzoates Chain transfer Equilibrium Free radicals Mass spectrometry Microreactors Molecular weight Monitoring NMR Nuclear magnetic resonance Polymerization Scientific imaging Shift reaction Software Solvents Spectroscopy |
| Title | Mapping Dithiobenzoate-Mediated RAFT Polymerization Products via Online Microreactor/Mass Spectrometry Monitoring |
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