Synthesis of a fluorescent BODIPY-tagged ROMP catalyst and initial polymerization-propelled diffusion studies

The synthesis of a Ru-based olefin metathesis catalyst dye-tagged at the N-heterocyclic carbene ligand is reported. Its catalytic activity toward ring-opening metathesis polymerization (ROMP) of 1,5-cyclooctadiene was found to be similar to that of its parent second-generation Hoveyda–Grubbs catalys...

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Bibliographic Details
Published in:Tetrahedron 2015-09, Vol.71 (35), p.5965-5972
Main Authors: Godoy, Jazmin, García-López, Víctor, Wang, Lin-Yung, Rondeau-Gagné, Simon, Link, Stephan, Martí, Angel A., Tour, James M.
Format: Article
Language:English
Subjects:
BODIPY
Diffusion coefficient
Fluorescence correlation spectroscopy
Fluorescent Hoveyda–Grubbs catalyst
Nanomachines
Ring-opening metathesis polymerization
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Summary:The synthesis of a Ru-based olefin metathesis catalyst dye-tagged at the N-heterocyclic carbene ligand is reported. Its catalytic activity toward ring-opening metathesis polymerization (ROMP) of 1,5-cyclooctadiene was found to be similar to that of its parent second-generation Hoveyda–Grubbs catalyst. The quantum yield of fluorescence (ΦF=0.22) makes it a good candidate to explore, by fluorescence correlation spectroscopy, the potential of a ROMP process to provide a molecule with sufficient energy for self-propulsion in solution. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.04.027