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

Jazmin Godoy; Víctor García-López; Lin Yung Wang; Simon Rondeau-Gagné; Stephan Link; Angel A. Martí; James M. Tour

doi:10.1016/j.tet.2015.04.027

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

Jazmin Godoy, Víctor García-López, Lin Yung Wang, Simon Rondeau-Gagné, Stephan Link, Angel A. Martí, James M. Tour

Research output: Contribution to journal › Article › peer-review

Abstract

Abstract 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 (Φ_F=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.

Original language	English (US)
Article number	26630
Pages (from-to)	5965-5972
Number of pages	8
Journal	Tetrahedron
Volume	71
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2015.04.027
State	Published - Jul 25 2015
Externally published	Yes

Keywords

BODIPY
Diffusion coefficient
Fluorescence correlation spectroscopy
Fluorescent Hoveyda-Grubbs catalyst
Nanomachines
Ring-opening metathesis polymerization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Online availability

10.1016/j.tet.2015.04.027

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title = "Synthesis of a fluorescent BODIPY-tagged ROMP catalyst and initial polymerization-propelled diffusion studies",

abstract = "Abstract 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.",

keywords = "BODIPY, Diffusion coefficient, Fluorescence correlation spectroscopy, Fluorescent Hoveyda-Grubbs catalyst, Nanomachines, Ring-opening metathesis polymerization",

author = "Jazmin Godoy and V{\'i}ctor Garc{\'i}a-L{\'o}pez and Wang, {Lin Yung} and Simon Rondeau-Gagn{\'e} and Stephan Link and Mart{\'i}, {Angel A.} and Tour, {James M.}",

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doi = "10.1016/j.tet.2015.04.027",

language = "English (US)",

volume = "71",

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T1 - Synthesis of a fluorescent BODIPY-tagged ROMP catalyst and initial polymerization-propelled diffusion studies

AU - Godoy, Jazmin

AU - García-López, Víctor

AU - Wang, Lin Yung

AU - Rondeau-Gagné, Simon

AU - Link, Stephan

AU - Martí, Angel A.

AU - Tour, James M.

PY - 2015/7/25

Y1 - 2015/7/25

N2 - Abstract 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.

AB - Abstract 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.

KW - BODIPY

KW - Diffusion coefficient

KW - Fluorescence correlation spectroscopy

KW - Fluorescent Hoveyda-Grubbs catalyst

KW - Nanomachines

KW - Ring-opening metathesis polymerization

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DO - 10.1016/j.tet.2015.04.027

M3 - Article

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SN - 0040-4020

VL - 71

SP - 5965

EP - 5972

JO - Tetrahedron

JF - Tetrahedron

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M1 - 26630

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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