Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Tricyclononenes and tricyclononadienes as efficient monomers for controlled ROMP: understanding structure–propagation rate relationships and enabling facile post-polymerization modification

Journal Article · · Chemical Science
DOI:https://doi.org/10.1039/D4SC01986E· OSTI ID:2352764
 [1];  [2];  [2];  [3]
  1. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
  2. Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA
  3. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Koch Institute for Integrative Cancer Research, Massachusetts Institute of Technology, 500 Main Street, Cambridge, MA 02139, USA, Broad Institute of MIT and Harvard, Cambridge, MA, 02142, USA

A tricyclononene and tricyclononadiene monomer library is studied experimentally and computationally to deepen understanding of structure propagation rate relationships in ROMP. A novel poly(tricyclononadiene) post-ROMP functionalization is explored.

Research Organization:
Univ. of Illinois at Urbana-Champaign, IL (United States)
Sponsoring Organization:
USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0023457
OSTI ID:
2352764
Alternate ID(s):
OSTI ID: 2472280
Journal Information:
Chemical Science, Journal Name: Chemical Science Journal Issue: 22 Vol. 15; ISSN 2041-6520; ISSN CSHCBM
Publisher:
Royal Society of Chemistry (RSC)Copyright Statement
Country of Publication:
United Kingdom
Language:
English

References (47)

A Practical and Highly Active Ruthenium-Based Catalyst that Effects the Cross Metathesis of Acrylonitrile journal November 2002
Synthesis of Functional Polymers by Post-Polymerization Modification journal November 2008
Synthesis and Gas-Transport Properties of Metathesis Polytricyclononenes Bearing Three Me 3 Si Groups per Monomer Unit journal July 2016
AQME: Automated quantum mechanical environments for researchers and educators journal February 2023
Comparative Reactivity of Me3Si-substituted Norbornene Derivatives in Ring-Opening Metathesis Polymerization journal December 2014
High pressure sequential (π2 + π2 + π2) and (π2 + σ2 + σ2) cycloaddition reactions. Synthesis of polycyclic bisadducts from C7H8 hydrocarbons journal January 1987
A new cycloadduct based on quadricyclane and perfluorocyclohexene: synthesis, metathesis polymerization and gas-transport properties of the obtained polymer journal March 2016
Metathesis-type poly-exo-tricyclononenes with fluoroorganic side substituents: Synthesis and gas-transport properties journal September 2018
The Development of Multidimensional Analysis Tools for Asymmetric Catalysis and Beyond journal May 2016
Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study journal November 2021
User Guide to Ring-Opening Metathesis Polymerization of endo-Norbornene Monomers with Chelated Initiators journal July 2022
Influence of the Norbornene Anchor Group in Ru-Mediated Ring-Opening Metathesis Polymerization: Synthesis of Linear Polymers journal May 2023
Influence of the Norbornene Anchor Group in Ru-Mediated Ring-Opening Metathesis Polymerization: Synthesis of Bottlebrush Polymers journal May 2023
ABA Triblock Brush Polymers: Synthesis, Self-Assembly, Conductivity, and Rheological Properties journal July 2015
Polyethylene as a Cosolvent and Catalyst Support in Ring-Opening Metathesis Polymerization journal August 2015
Pendant Group Modifications Provide Graft Copolymer Silicones with Exceptionally Broad Thermomechanical Properties journal December 2022
Exo -selective, Reductive Heck Derived Polynorbornenes with Enhanced Molecular Weights, Yields, and Hydrocarbon Gas Transport Properties journal August 2020
Equilibrium acidities in dimethyl sulfoxide solution journal December 1988
The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry journal September 2013
Regio- and stereospecific [2.pi. + 2.sigma. + 2.sigma.] cycloaddition reaction of quadricyclane journal February 1972
Cycloaddition Reactions of “Quadricyclanes”1 journal September 1966
Scope of the Ring-Opening Metathesis Polymerization (ROMP) Reaction of 1-Substituted Cyclobutenes journal August 2010
Synthesis of Copolymers by Alternating ROMP (AROMP) journal March 2009
A Cyclic Ruthenium Benzylidene Initiator Platform Enhances Reactivity for Ring-Expansion Metathesis Polymerization journal May 2021
A Comprehensive Discovery Platform for Organophosphorus Ligands for Catalysis journal January 2022
Bottlebrush Polymer Synthesis by Ring-Opening Metathesis Polymerization: The Significance of the Anchor Group journal May 2016
Design, Synthesis, and Self-Assembly of Polymers with Tailored Graft Distributions journal November 2017
Examining the Effects of Monomer and Catalyst Structure on the Mechanism of Ruthenium-Catalyzed Ring-Opening Metathesis Polymerization journal October 2019
Mechanistic and Kinetic Studies of the Ring Opening Metathesis Polymerization of Norbornenyl Monomers by a Grubbs Third Generation Catalyst journal October 2019
Equilibrium acidities and homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in N-substituted trimethylammonium and pyridinium cations journal May 1993
New Polymers from Ring-Opening Metathesis Polymerization of Quadricyclane Adducts journal June 1995
A Combined Experimental and Theoretical Study Examining the Binding of N -Heterocyclic Carbenes (NHC) to the Cp*RuCl (Cp* = η 5 -C 5 Me 5 ) Moiety:  Insight into Stereoelectronic Differences between Unsaturated and Saturated NHC Ligands journal October 2003
Metathesis and addition polymerization of novel Me3Si- and Me3Ge-substituted tricyclononenes journal December 2012
The preparation of well-controlled poly(N-cyclohexyl-exo-norbornene-5,6-dicarboximide) polymers journal May 2014
Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis journal January 2010
Investigation into thiol-(meth)acrylate Michael addition reactions using amine and phosphine catalysts journal January 2010
Predictive and mechanistic multivariate linear regression models for reaction development journal January 2018
Janus tricyclononene polymers bearing tri( n -alkoxy)silyl side groups for membrane gas separation journal January 2018
Ring-opening metathesis polymerization of norbornene–benzoladderene (macro)monomers journal January 2023
The Preparation of Stereoisomeric Tricyclo[4.2.1.02,5]nona-7-ene-3,4-dicar­boximides and Anhydrides: Literature Corrections and New Products journal May 2014
Photolysis of Fused Cyclobutatriazolines: An Adventitious Route to 3,6-Di(2-pyridyl)pyridazonorbornadiene journal January 2000
Synthesis and gas-separation properties of metathesis poly(3-fluoro-3-pentafluoroethyl-4,4-bis(trifluoromethyl)tricyclonene-7) journal November 2015
Polymerization of Tricyclononenes journal September 2019
Synthetic Chemistry of Quadricyclane journal May 2006
Chromatographic Method for Evaluation of Polymeric GC Stationary Phases Ageing Using the Novel Non-Cross-Linked Poly(3-(Tributoxysilyl)Tricyclononene-7) as the Model Stationary Phase journal June 2021
Impact of the Polymer Backbone Structure on the Separation Properties of New Stationary Phases Based on Tricyclononenes journal November 2022
Selective ring-opening metathesis polymerization (ROMP) of cyclobutenes. Unsymmetrical ladderphane containing polycyclobutene and polynorbornene strands journal January 2019

Similar Records

Proof of Tacticity of Stereoregular ROMP Polymers through Post Polymerization Modification
Journal Article · Wed Apr 22 20:00:00 EDT 2015 · Macromolecules · OSTI ID:1557797

Tuning the Reactivity of Cyclopropenes from Living Ring‐Opening Metathesis Polymerization (ROMP) to Single‐Addition and Alternating ROMP
Journal Article · Mon Oct 21 20:00:00 EDT 2019 · Angewandte Chemie (International Edition) · OSTI ID:1571331