Journal
ORGANOMETALLICS
Volume 29, Issue 1, Pages 117-124Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om900857w
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Funding
- Polish Ministry of Science and Higher Education [N204157636]
- Foundation for Polish Science
- SRL
- Polymer Competence Center Leoben GmbH (PCCL, Austria)
- Austrian Ministry of Traffic, Innovation and Technology
- European Community [CPFP 211468-2 EUMET]
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The synthesis and characterization of two ruthenium complexes bearing chelating carbene ligands is described. Carbene precursors, 2-(2-vinylphenyl)pyridine and 10-vinylbenzo[h]quinoline, are applied to prepare (SPY-5-3l)-diChloro-(k(2)(C,N)-N-2-(2-vinylbenzylidene)pyridine(1,3-bis(2,4, 6-trimethylphenyl)4,5-dihydroimidazol-2-ylidene)ruthenium (VIII)and (SPY-5-3l)-dichloro-(k(2)(C,N)-2-(benzo[h]quinolin- 10-yl)methylidene)(1,3-bis(2,4,6-trimethylphenyl)4,5-dihydroimidazol-2-ylidene)-ruthenium (IX). Both catalysts/initiators are used to perform ring-closing metathesis (RCM) and ring-opening metathesis polymerizations (ROMP). RCM experiments reveal significant thermal stability of the catalysts under forcing reaction conditions such as boiling toluene for 48 h. Even challenging substrates such as diethylallyl(2-methylallyl)malonate are completely transformed with low catalyst loadings (0.1 mol % at 110 degrees C), The high thermal stability, i.e., latency, might be explained by a slow generation of the catalytically active methylidene species. This feature leads to high molecular weight polymers and a thermal switchability in ROMP. Initiation of polymerizations of several norbornene derivatives occurs at about 48 +/- 5 degrees C in the case of initiator VIII and at 110 +/- 9 degrees C in the case of IX. A substantial increase of the switching temperature in the following cases could be supported with higher rigidity of the chelating carbene moiety in IX when compared to VIII.
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