Bottlebrush Polymer Synthesis by Ring-Opening Metathesis Polymerization: The Significance of the Anchor Group
Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition between the kinetics of the polymerization and the lifetime of the catalyst. We evaluated the effect of anchor group chemistrythe configuration o...
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| Published in | Journal of the American Chemical Society Vol. 138; no. 22; pp. 6998 - 7004 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
08.06.2016
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition between the kinetics of the polymerization and the lifetime of the catalyst. We evaluated the effect of anchor group chemistrythe configuration of atoms linking the polymer to a polymerizable norborneneon the kinetics of ROMP of polystyrene and poly(lactic acid) MMs initiated by (H2IMes)(pyr)2(Cl)2RuCHPh (Grubbs third generation catalyst). We observed a variance in the rate of propagation of >4-fold between similar MMs with different anchor groups. This phenomenon was conserved across all MMs tested, regardless of solvent, molecular weight (MW), or repeat unit identity. The observed >4-fold difference in propagation rate had a dramatic effect on the maximum obtainable backbone degree of polymerization, with slower propagating MMs reducing the maximum bottlebrush MW by an order of magnitude (from ∼106 to ∼105 Da). A chelation mechanism was initially proposed to explain the observed anchor group effect, but experimental and computational studies indicated that the rate differences likely resulted from a combination of varying steric demands and electronic structure among the different anchor groups. The addition of trifluoroacetic acid to the ROMP reaction substantially increased the propagation rate for all anchor groups tested, likely due to scavenging of the pyridine ligands. Based on these data, rational selection of the anchor group is critical to achieve high MM conversion and to prepare pure, high MW bottlebrush polymers by ROMP grafting-through. |
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| AbstractList | Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition between the kinetics of the polymerization and the lifetime of the catalyst. We evaluated the effect of anchor group chemistry-the configuration of atoms linking the polymer to a polymerizable norbornene-on the kinetics of ROMP of polystyrene and poly(lactic acid) MMs initiated by (H2IMes)(pyr)2(Cl)2Ru═CHPh (Grubbs third generation catalyst). We observed a variance in the rate of propagation of >4-fold between similar MMs with different anchor groups. This phenomenon was conserved across all MMs tested, regardless of solvent, molecular weight (MW), or repeat unit identity. The observed >4-fold difference in propagation rate had a dramatic effect on the maximum obtainable backbone degree of polymerization, with slower propagating MMs reducing the maximum bottlebrush MW by an order of magnitude (from ∼10(6) to ∼10(5) Da). A chelation mechanism was initially proposed to explain the observed anchor group effect, but experimental and computational studies indicated that the rate differences likely resulted from a combination of varying steric demands and electronic structure among the different anchor groups. The addition of trifluoroacetic acid to the ROMP reaction substantially increased the propagation rate for all anchor groups tested, likely due to scavenging of the pyridine ligands. Based on these data, rational selection of the anchor group is critical to achieve high MM conversion and to prepare pure, high MW bottlebrush polymers by ROMP grafting-through. Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition between the kinetics of the polymerization and the lifetime of the catalyst. We evaluated the effect of anchor group chemistrythe configuration of atoms linking the polymer to a polymerizable norborneneon the kinetics of ROMP of polystyrene and poly(lactic acid) MMs initiated by (H₂IMes)(pyr)₂(Cl)₂RuCHPh (Grubbs third generation catalyst). We observed a variance in the rate of propagation of >4-fold between similar MMs with different anchor groups. This phenomenon was conserved across all MMs tested, regardless of solvent, molecular weight (MW), or repeat unit identity. The observed >4-fold difference in propagation rate had a dramatic effect on the maximum obtainable backbone degree of polymerization, with slower propagating MMs reducing the maximum bottlebrush MW by an order of magnitude (from ∼10⁶ to ∼10⁵ Da). A chelation mechanism was initially proposed to explain the observed anchor group effect, but experimental and computational studies indicated that the rate differences likely resulted from a combination of varying steric demands and electronic structure among the different anchor groups. The addition of trifluoroacetic acid to the ROMP reaction substantially increased the propagation rate for all anchor groups tested, likely due to scavenging of the pyridine ligands. Based on these data, rational selection of the anchor group is critical to achieve high MM conversion and to prepare pure, high MW bottlebrush polymers by ROMP grafting-through. Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition between the kinetics of the polymerization and the lifetime of the catalyst. We evaluated the effect of anchor group chemistrythe configuration of atoms linking the polymer to a polymerizable norborneneon the kinetics of ROMP of polystyrene and poly(lactic acid) MMs initiated by (H2IMes)(pyr)2(Cl)2RuCHPh (Grubbs third generation catalyst). We observed a variance in the rate of propagation of >4-fold between similar MMs with different anchor groups. This phenomenon was conserved across all MMs tested, regardless of solvent, molecular weight (MW), or repeat unit identity. The observed >4-fold difference in propagation rate had a dramatic effect on the maximum obtainable backbone degree of polymerization, with slower propagating MMs reducing the maximum bottlebrush MW by an order of magnitude (from ∼106 to ∼105 Da). A chelation mechanism was initially proposed to explain the observed anchor group effect, but experimental and computational studies indicated that the rate differences likely resulted from a combination of varying steric demands and electronic structure among the different anchor groups. The addition of trifluoroacetic acid to the ROMP reaction substantially increased the propagation rate for all anchor groups tested, likely due to scavenging of the pyridine ligands. Based on these data, rational selection of the anchor group is critical to achieve high MM conversion and to prepare pure, high MW bottlebrush polymers by ROMP grafting-through. Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition between the kinetics of the polymerization and the lifetime of the catalyst. We evaluated the effect of anchor group chemistry-the configuration of atoms linking the polymer to a polymerizable norbornene-on the kinetics of ROMP of polystyrene and poly(lactic acid) MMs initiated by (H2IMes)(pyr)2(Cl)2Ru═CHPh (Grubbs third generation catalyst). We observed a variance in the rate of propagation of >4-fold between similar MMs with different anchor groups. This phenomenon was conserved across all MMs tested, regardless of solvent, molecular weight (MW), or repeat unit identity. The observed >4-fold difference in propagation rate had a dramatic effect on the maximum obtainable backbone degree of polymerization, with slower propagating MMs reducing the maximum bottlebrush MW by an order of magnitude (from ∼10(6) to ∼10(5) Da). A chelation mechanism was initially proposed to explain the observed anchor group effect, but experimental and computational studies indicated that the rate differences likely resulted from a combination of varying steric demands and electronic structure among the different anchor groups. The addition of trifluoroacetic acid to the ROMP reaction substantially increased the propagation rate for all anchor groups tested, likely due to scavenging of the pyridine ligands. Based on these data, rational selection of the anchor group is critical to achieve high MM conversion and to prepare pure, high MW bottlebrush polymers by ROMP grafting-through.Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition between the kinetics of the polymerization and the lifetime of the catalyst. We evaluated the effect of anchor group chemistry-the configuration of atoms linking the polymer to a polymerizable norbornene-on the kinetics of ROMP of polystyrene and poly(lactic acid) MMs initiated by (H2IMes)(pyr)2(Cl)2Ru═CHPh (Grubbs third generation catalyst). We observed a variance in the rate of propagation of >4-fold between similar MMs with different anchor groups. This phenomenon was conserved across all MMs tested, regardless of solvent, molecular weight (MW), or repeat unit identity. The observed >4-fold difference in propagation rate had a dramatic effect on the maximum obtainable backbone degree of polymerization, with slower propagating MMs reducing the maximum bottlebrush MW by an order of magnitude (from ∼10(6) to ∼10(5) Da). A chelation mechanism was initially proposed to explain the observed anchor group effect, but experimental and computational studies indicated that the rate differences likely resulted from a combination of varying steric demands and electronic structure among the different anchor groups. The addition of trifluoroacetic acid to the ROMP reaction substantially increased the propagation rate for all anchor groups tested, likely due to scavenging of the pyridine ligands. Based on these data, rational selection of the anchor group is critical to achieve high MM conversion and to prepare pure, high MW bottlebrush polymers by ROMP grafting-through. |
| Author | Chapleski, Robert C Foster, Jeffrey C Troya, Diego Radzinski, Scott C Matson, John B |
| AuthorAffiliation | Department of Chemistry Macromolecules Innovation Institute Virginia Tech |
| AuthorAffiliation_xml | – name: Virginia Tech – name: Macromolecules Innovation Institute – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Scott C surname: Radzinski fullname: Radzinski, Scott C organization: Virginia Tech – sequence: 2 givenname: Jeffrey C surname: Foster fullname: Foster, Jeffrey C organization: Virginia Tech – sequence: 3 givenname: Robert C surname: Chapleski fullname: Chapleski, Robert C organization: Virginia Tech – sequence: 4 givenname: Diego surname: Troya fullname: Troya, Diego email: troya@vt.edu organization: Virginia Tech – sequence: 5 givenname: John B surname: Matson fullname: Matson, John B email: jbmatson@vt.edu organization: Virginia Tech |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27219866$$D View this record in MEDLINE/PubMed |
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| Snippet | Control over bottlebrush polymer synthesis by ring-opening metathesis polymerization (ROMP) of macromonomers (MMs) is highly dependent on the competition... |
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| SubjectTerms | catalysts chelation group effect ligands molecular weight polylactic acid polymerization pyridines solvents variance |
| Title | Bottlebrush Polymer Synthesis by Ring-Opening Metathesis Polymerization: The Significance of the Anchor Group |
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