User Guide to Ring-Opening Metathesis Polymerization of endo -Norbornene Monomers with Chelated Initiators

Cater, Henry L.; Balynska, Iana; Allen, Marshall J.; Freeman, Benny D.; Page, Zachariah A.

doi:10.1021/acs.macromol.2c01196

User Guide to Ring-Opening Metathesis Polymerization of endo -Norbornene Monomers with Chelated Initiators

Journal Article · 26 July 2022 · Macromolecules

DOI:https://doi.org/10.1021/acs.macromol.2c01196· OSTI ID:1978165

Cater, Henry L. ^[1]; Balynska, Iana ^[1]; Allen, Marshall J. ^[2]; ^[2]; ^[1]

Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, United States
McKetta Department of Chemical Engineering, The University of Texas at Austin, Austin, Texas 78712, United States

Not provided.

Research Organization:: Univ. of Texas, Austin, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0019272

OSTI ID:: 1978165

Journal Information:: Macromolecules, Vol. 55, Issue 15; ISSN 0024-9297

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (59)

Bioinspired structural materials Wegst, Ulrike G. K.; Bai, Hao; Saiz, Eduardo Nature Materials, Vol. 14, Issue 1 https://doi.org/10.1038/nmat4089	journal	October 2014
Soft Materials by Design: Unconventional Polymer Networks Give Extreme Properties Zhao, Xuanhe; Chen, Xiaoyu; Yuk, Hyunwoo Chemical Reviews, Vol. 121, Issue 8 https://doi.org/10.1021/acs.chemrev.0c01088	journal	April 2021
Biological and bioinspired materials: Structure leading to functional and mechanical performance Wang, Yayun; Naleway, Steven E.; Wang, Bin Bioactive Materials, Vol. 5, Issue 4 https://doi.org/10.1016/j.bioactmat.2020.06.003	journal	December 2020
50th Anniversary Perspective : Living Polymerization—Emphasizing the Molecule in Macromolecules Grubbs, Robert B.; Grubbs, Robert H. Macromolecules, Vol. 50, Issue 18 https://doi.org/10.1021/acs.macromol.7b01440	journal	September 2017
The ROMP toolbox upgraded Leitgeb, Anita; Wappel, Julia; Slugovc, Christian Polymer, Vol. 51, Issue 14, p. 2927-2946 https://doi.org/10.1016/j.polymer.2010.05.002	journal	June 2010
Catalytic living ring-opening metathesis polymerization with Grubbs’ second- and third-generation catalysts Yasir, Mohammad; Liu, Peng; Tennie, Iris K. Nature Chemistry, Vol. 11, Issue 5 https://doi.org/10.1038/s41557-019-0239-4	journal	April 2019
Flow-facilitated ring opening metathesis polymerization (ROMP) and post-polymerization modification reactions Subnaik, Selesha I.; Hobbs, Christopher E. Polymer Chemistry, Vol. 10, Issue 33 https://doi.org/10.1039/C9PY00822E	journal	January 2019
Manipulating the ABCs of self-assembly via low-χ block polymer design Chang, Alice B.; Bates, Christopher M.; Lee, Byeongdu Proceedings of the National Academy of Sciences, Vol. 114, Issue 25 https://doi.org/10.1073/pnas.1701386114	journal	June 2017
ABA Triblock Brush Polymers: Synthesis, Self-Assembly, Conductivity, and Rheological Properties Bates, Christopher M.; Chang, Alice B.; Momčilović, Nebojša Macromolecules, Vol. 48, Issue 14 https://doi.org/10.1021/acs.macromol.5b00880	journal	July 2015
Design, Synthesis, and Self-Assembly of Polymers with Tailored Graft Distributions Chang, Alice B.; Lin, Tzu-Pin; Thompson, Niklas B. Journal of the American Chemical Society, Vol. 139, Issue 48 https://doi.org/10.1021/jacs.7b10525	journal	November 2017
Outstanding dielectric and thermal properties of main chain-type poly(benzoxazine- co -imide- co -siloxane)-based cross-linked networks Zhang, Kan; Yu, Xinye; Kuo, Shiao-Wei Polymer Chemistry, Vol. 10, Issue 19 https://doi.org/10.1039/C9PY00464E	journal	January 2019
Phenothiazine‐Functionalized Poly(norbornene)s as High‐Rate Cathode Materials for Organic Batteries Otteny, Fabian; Studer, Gauthier; Kolek, Martin ChemSusChem, Vol. 13, Issue 9 https://doi.org/10.1002/cssc.201903168	journal	January 2020
Electro-optic properties of a side chain poly(norbornene-dicarboximide) system with an appended phenyl vinylene thiophene chromophore Spring, Andrew M.; Qiu, Feng; Hong, Jianxun Polymer, Vol. 119 https://doi.org/10.1016/j.polymer.2017.05.005	journal	June 2017
Impact of backbone composition on homopolymer dynamics and brush block copolymer self-assembly Boyle, Bret M.; Collins, Joseph L.; Mensch, Tara E. Polymer Chemistry, Vol. 11, Issue 45 https://doi.org/10.1039/D0PY01007C	journal	January 2020
Synthesis of penicillin derived polymers utilising ring-opening metathesis polymerisation methodology Biagini, Stefano C. G.; Gibson, Vernon C.; Giles, Matthew R. Chemical Communications, Issue 12 https://doi.org/10.1039/a701494e	journal	January 1997
Recent advances in ring-opening metathesis polymerization, and application to synthesis of functional materials Sutthasupa, Sutthira; Shiotsuki, Masashi; Sanda, Fumio Polymer Journal, Vol. 42, Issue 12 https://doi.org/10.1038/pj.2010.94	journal	October 2010
Ring-opening metathesis polymerization-induced self-assembly (ROMPISA) Varlas, Spyridon; Foster, Jeffrey C.; O'Reilly, Rachel K. Chemical Communications, Vol. 55, Issue 62 https://doi.org/10.1039/C9CC04445K	journal	January 2019
Synthesis and properties of poly(norbornene)s with lateral aramid groups Kong, Phally; Drechsler, Susanne; Balog, Sandor Polymer Chemistry, Vol. 10, Issue 16 https://doi.org/10.1039/C9PY00187E	journal	January 2019
Polymerization of protecting-group-free peptides via ROMP Kammeyer, Jacquelin K.; Blum, Angela P.; Adamiak, Lisa Polymer Chemistry, Vol. 4, Issue 14 https://doi.org/10.1039/c3py00526g	journal	January 2013
Brush-First and ROMP-Out with Functional (Macro)monomers: Method Development, Structural Investigations, and Applications of an Expanded Brush-Arm Star Polymer Platform Golder, Matthew R.; Nguyen, Hung V. -T.; Oldenhuis, Nathan J. Macromolecules, Vol. 51, Issue 23 https://doi.org/10.1021/acs.macromol.8b01966	journal	November 2018
Brush‐First ROMP of poly(ethylene oxide) macromonomers of varied length: impact of polymer architecture on thermal behavior and Li ⁺ conductivity Shibuya, Yoshiki; Tatara, Ryoichi; Jiang, Yivan Journal of Polymer Science Part A: Polymer Chemistry, Vol. 57, Issue 3 https://doi.org/10.1002/pola.29242	journal	September 2018
Examining the Effects of Monomer and Catalyst Structure on the Mechanism of Ruthenium-Catalyzed Ring-Opening Metathesis Polymerization Wolf, William J.; Lin, Tzu-Pin; Grubbs, Robert H. Journal of the American Chemical Society, Vol. 141, Issue 44 https://doi.org/10.1021/jacs.9b08835	journal	October 2019
The Resting State Makes the Difference: The Influence of the Anchor Group in the ROMP of Norbornene Derivatives Slugovc, Christian; Demel, Sandra; Riegler, Silvia Macromolecular Rapid Communications, Vol. 25, Issue 3 https://doi.org/10.1002/marc.200300196	journal	February 2004
One-Shot Synthesis and Melt Self-Assembly of Bottlebrush Copolymers with a Gradient Compositional Profile Jiang, Liuyin; Nykypanchuk, Dmytro; Ribbe, Alexander E. ACS Macro Letters, Vol. 7, Issue 6 https://doi.org/10.1021/acsmacrolett.8b00273	journal	May 2018
Comparative Reactivity of E xo - and E ndo -Isomers in the Ru-Initiated Ring-Opening Metathesis Polymerization of Doubly Functionalized Norbornenes with Both Cyano and Ester Groups Nishihara, Yasushi; Inoue, Yoshiaki; Nakayama, Yuushou Macromolecules, Vol. 39, Issue 22 https://doi.org/10.1021/ma061781c	journal	October 2006
Ring‐Opening Metathesis Polymerization of endo ‐ and exo ‐Norbornene Lactones Miyasako, Narumi; Matsuoka, Shin‐ichi; Suzuki, Masato Macromolecular Rapid Communications, Vol. 42, Issue 8 https://doi.org/10.1002/marc.202170027	journal	April 2021
Synthesis and characterization of hydrogenated poly(norbornene endo-dicarboximide)s prepared by ring opening metathesis polymerization Yoon, Kyung-Hwan; Kim, Kyung Oh; Schaefer, Mark Polymer, Vol. 53, Issue 11 https://doi.org/10.1016/j.polymer.2012.02.047	journal	May 2012
Living Polymerization of Monomers Containing endo-Tricyclo[4.2.2.0^2,5]deca-3,9-diene Using Second Generation Grubbs and Hoveyda–Grubbs Catalysts: Approach to Synthesis of Well-Defined Star Polymers Kim, Kyung Oh; Shin, Suyong; Kim, Junyong Macromolecules, Vol. 47, Issue 4 https://doi.org/10.1021/ma5000333	journal	February 2014
Ring-opening metathesis polymerization of cis-5-norbornene-endo-2,3-dicarboxylic anhydride derivatives using the grubbs third generation catalyst Yang, Ji-xing; Ren, Li-xia; Li, Yue-sheng Chinese Journal of Polymer Science, Vol. 35, Issue 1 https://doi.org/10.1007/s10118-017-1873-1	journal	November 2016
The preparation of well-controlled poly(N-cyclohexyl-exo-norbornene-5,6-dicarboximide) polymers Spring, Andrew M.; Yu, Feng; Qiu, Feng Polymer Journal, Vol. 46, Issue 9 https://doi.org/10.1038/pj.2014.26	journal	May 2014
Intra-chain radical chemistry as a route to poly(norbornene imide) single-chain nanoparticles: structural considerations and the role of adventitious oxygen Cole, Justin P.; Lessard, Jacob J.; Lyon, Christopher K. Polymer Chemistry, Vol. 6, Issue 31 https://doi.org/10.1039/C5PY00265F	journal	January 2015
Synthesis of Fluorine-18 Functionalized Nanoparticles for use as in vivo Molecular Imaging Agents Matson, John B.; Grubbs, Robert H. Journal of the American Chemical Society, Vol. 130, Issue 21 https://doi.org/10.1021/ja802010d	journal	May 2008
Poly(phenylnorbornene) from Ring-Opening Metathesis and Its Hydrogenated Derivatives Li, Sheng; Burns, Adam B.; Register, Richard A. Macromolecular Chemistry and Physics, Vol. 213, Issue 19 https://doi.org/10.1002/macp.201200294	journal	August 2012
Decomposition of Ruthenium Olefin Metathesis Catalysts Hong, Soon Hyeok; Wenzel, Anna G.; Salguero, Tina T. Journal of the American Chemical Society, Vol. 129, Issue 25 https://doi.org/10.1021/ja0713577	journal	June 2007
A Recyclable Ru-Based Metathesis Catalyst Kingsbury, Jason S.; Harrity, Joseph P. A.; Bonitatebus, Peter J. Journal of the American Chemical Society, Vol. 121, Issue 4 https://doi.org/10.1021/ja983222u	journal	February 1999
Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts Garber, Steven B.; Kingsbury, Jason S.; Gray, Brian L. Journal of the American Chemical Society, Vol. 122, Issue 34 https://doi.org/10.1021/ja001179g	journal	August 2000
Ring-Opening Metathesis Polymerization with the Second Generation Hoveyda–Grubbs Catalyst: An Efficient Approach toward High-Purity Functionalized Macrocyclic Oligo(cyclooctene)s Blencowe, Anton; Qiao, Greg G. Journal of the American Chemical Society, Vol. 135, Issue 15, p. 5717-5725 https://doi.org/10.1021/ja312418z	journal	April 2013
Highly active ruthenium metathesis catalysts enabling ring-opening metathesis polymerization of cyclopentadiene at low temperatures Song, Kitaek; Kim, Kunsoon; Hong, Daeun Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-11806-5	journal	August 2019
Dewar lactone as a modular platform to a new class of substituted poly(acetylene)s Seo, Jinwon; Lee, Stanfield Y.; Bielawski, Christopher W. Polymer Chemistry, Vol. 10, Issue 47 https://doi.org/10.1039/C9PY01282F	journal	January 2019
Catalytic Living Ring Opening Metathesis Polymerisation: The Importance of Ring Strain in Chain Transfer Agents Liu, Peng; Yasir, Mohammad; Kilbinger, Andreas F. M. Angewandte Chemie International Edition, Vol. 58, Issue 43 https://doi.org/10.1002/anie.201907921	journal	September 2019
Mono-telechelic polymers by catalytic living ring-opening metathesis polymerization with second-generation Hoveyda–Grubbs catalyst Liu, Peng; Dong, Zhenghao; Kilbinger, Andreas F. M. Materials Chemistry Frontiers, Vol. 4, Issue 9 https://doi.org/10.1039/D0QM00417K	journal	January 2020
Metal-Free Ring-Opening Metathesis Polymerization Ogawa, Kelli A.; Goetz, Adam E.; Boydston, Andrew J. Journal of the American Chemical Society, Vol. 137, Issue 4 https://doi.org/10.1021/ja512073m	journal	January 2015
Metal-Free Ring-Opening Metathesis Polymerization: From Concept to Creation Lu, Pengtao; Kensy, Victoria K.; Tritt, Rachel L. Accounts of Chemical Research, Vol. 53, Issue 10 https://doi.org/10.1021/acs.accounts.0c00427	journal	September 2020
A Practical and Highly Active Ruthenium-Based Catalyst that Effects the Cross Metathesis of Acrylonitrile Love, Jennifer A.; Morgan, John P.; Trnka, Tina M. Angewandte Chemie International Edition, Vol. 41, Issue 21 https://doi.org/10.1002/1521-3773(20021104)41:21<4035::AID-ANIE4035>3.0.CO;2-I	journal	November 2002
Olefin metathesis in air Piola, Lorenzo; Nahra, Fady; Nolan, Steven P. Beilstein Journal of Organic Chemistry, Vol. 11 https://doi.org/10.3762/bjoc.11.221	journal	October 2015
Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis Hoveyda, Amir H.; Gillingham, Dennis G.; Van Veldhuizen, Joshua J. Organic & Biomolecular Chemistry, Vol. 2, Issue 1 https://doi.org/10.1039/b311496c	journal	January 2004
Mechanistic investigation of the ring opening metathesis polymerisation of alkoxy and alkyl substituted paracyclophanedienes Kumar, Dharam R.; Lidster, Benjamin J.; Adams, Ralph W. Polymer Chemistry, Vol. 8, Issue 20 https://doi.org/10.1039/C7PY00543A	journal	January 2017
Increasing the Initiation Efficiency of Ruthenium-Based Ring-Opening Metathesis Initiators: Effect of Excess Phosphine Bielawski, Christopher W.; Grubbs, Robert H. Macromolecules, Vol. 34, Issue 26 https://doi.org/10.1021/ma011214j	journal	November 2001
Synthesis of Narrow-Distribution, High-Molecular-Weight ROMP Polycyclopentene via Suppression of Acyclic Metathesis Side Reactions Mulhearn, William D.; Register, Richard A. ACS Macro Letters, Vol. 6, Issue 2 https://doi.org/10.1021/acsmacrolett.6b00969	journal	January 2017
Decomposition of Ruthenium Olefin Metathesis Catalyst Jawiczuk, Magdalena; Marczyk, Anna; Trzaskowski, Bartosz Catalysts, Vol. 10, Issue 8 https://doi.org/10.3390/catal10080887	journal	August 2020
Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation Michrowska, Anna; Bujok, Robert; Harutyunyan, Syuzanna Journal of the American Chemical Society, Vol. 126, Issue 30 https://doi.org/10.1021/ja048794v	journal	August 2004
Nitro and Other Electron Withdrawing Group Activated Ruthenium Catalysts for Olefin Metathesis Reactions Kajetanowicz, Anna; Grela, Karol Angewandte Chemie International Edition, Vol. 60, Issue 25 https://doi.org/10.1002/anie.202008150	journal	December 2020
Making the family portrait complete: Synthesis of Electron Withdrawing Group activated Hoveyda-Grubbs catalysts bearing sulfone and ketone functionalities Bieniek, Michał; Bujok, Robert; Milewski, Mariusz Journal of Organometallic Chemistry, Vol. 918 https://doi.org/10.1016/j.jorganchem.2020.121276	journal	July 2020
A New, Highly Active Bimetallic Grubbs–Hoveyda–Blechert Precatalyst for Alkene Metathesis Vinokurov, Nikolai; Garabatos-Perera, José Ramon; Zhao-Karger, Zhirong Organometallics, Vol. 27, Issue 8 https://doi.org/10.1021/om701242t	journal	March 2008
An Initiation Kinetics Prediction Model Enables Rational Design of Ruthenium Olefin Metathesis Catalysts Bearing Modified Chelating Benzylidenes Luo, Shao-Xiong Lennon; Engle, Keary M.; Dong, Xiaofei ACS Catalysis, Vol. 8, Issue 5 https://doi.org/10.1021/acscatal.8b00843	journal	April 2018
A Highly Efficient Ruthenium Catalyst for Metathesis Reactions Grela, Karol; Harutyunyan, Syuzanna; Michrowska, Anna Angewandte Chemie International Edition, Vol. 41, Issue 21 https://doi.org/10.1002/1521-3773(20021104)41:21<4038::AID-ANIE4038>3.0.CO;2-0	journal	November 2002
A New Highly Efficient Ruthenium Metathesis Catalyst This work was supported by the Fonds der Chemischen Industrie. Wakamatsu, Hideaki; Blechert, Siegfried Angewandte Chemie International Edition, Vol. 41, Issue 13 https://doi.org/10.1002/1521-3773(20020703)41:13<2403::AID-ANIE2403>3.0.CO;2-F	journal	July 2002
Origins of Initiation Rate Differences in Ruthenium Olefin Metathesis Catalysts Containing Chelating Benzylidenes Engle, Keary M.; Lu, Gang; Luo, Shao-Xiong Lennon Journal of the American Chemical Society, Vol. 137, Issue 17 https://doi.org/10.1021/jacs.5b01144	journal	April 2015
Synthesis and structure-property comparisons of hydrogenated poly(oxanorbornene-imide)s and poly(norbornene-imide)s prepared by ring-opening metathesis polymerization Yoon, Kyung-Hwan; Kim, Kyung Oh; Wang, Chengqing Journal of Polymer Science Part A: Polymer Chemistry, Vol. 50, Issue 18 https://doi.org/10.1002/pola.26171	journal	June 2012

Similar Records

Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of Norbornene and Tetracyclododecene by Mo and W Initiators

Journal Article · 2015 · Macromolecules · OSTI ID:1557800

Autenrieth, Benjamin; Schrock, Richard R.

Ring-opening metathesis polymerization of norbornene by Cp{sup *}{sub 2}Os{sub 2}Br{sub 4} and related compounds

Journal Article · 1999 · Organometallics · OSTI ID:354375

Brumaghim, J L; Girolami, G S

Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of endo -Dicyclopentadiene by Molybdenum and Tungsten Catalysts

Journal Article · 2015 · Macromolecules · OSTI ID:1557801

Autenrieth, Benjamin; Jeong, Hyangsoo; Forrest, William P.; +5 more

Related Subjects

Polymer Science

User Guide to Ring-Opening Metathesis Polymerization of endo -Norbornene Monomers with Chelated Initiators

Citation Formats

References (59)

Similar Records

Related Subjects