Unraveling substituent effects on the glass transition temperatures of biorenewable polyesters

Yu, Xiaopeng; Jia, Junteng; Xu, Shu; Lao, Ka Un; Sanford, Maria J.; Ramakrishnan, Ramesh K.; Nazarenko, Sergei I.; Hoye, Thomas R.; Coates, Geoffrey W.; DiStasio, Jr., Robert A.

doi:10.1038/s41467-018-05269-3

Title: Unraveling substituent effects on the glass transition temperatures of biorenewable polyesters

Journal Article · 22 July 2018 · Nature Communications

DOI: https://doi.org/10.1038/s41467-018-05269-3 · OSTI ID:1543746

^[1]; Jia, Junteng ^[1];

^[2];

^[1];

^[1]; Ramakrishnan, Ramesh K. ^[3]; Nazarenko, Sergei I. ^[3];

^[2];

^[1];

^[1]

Cornell Univ., Ithaca, NY (United States)
Univ. of Minnesota, Minneapolis, MN (United States)
Univ. of Southern Mississippi, Hattiesburg, MS (United States)

Converting biomass-based feedstocks into polymers not only reduces our reliance on fossil fuels, but also furnishes multiple opportunities to design biorenewable polymers with targeted properties and functionalities. Here we report a series of high glass transition temperature (T_g up to 184°C) polyesters derived from sugar-based furan derivatives as well as a joint experimental and theoretical study of substituent effects on their thermal properties. Surprisingly, we find that polymers with moderate steric hindrance exhibit the highest T_g values. Through a detailed Ramachandran-type analysis of the rotational flexibility of the polymer backbone, we find that additional steric hindrance does not necessarily increase chain stiffness in these polyesters. We attribute this interesting structure-property relationship to a complex interplay between methyl-induced steric strain and the concerted rotations along the polymer backbone. We believe that our findings provide key insight into the relationship between structure and thermal properties across a range of synthetic polymers.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Univ. of California, Oakland, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1543746

Journal Information:: Nature Communications, Journal Name: Nature Communications Journal Issue: 1 Vol. 9; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

References (107)

Alternating Copolymerization of Propylene Oxide with Biorenewable Terpene-Based Cyclic Anhydrides: A Sustainable Route to Aliphatic Polyesters with High Glass Transition Temperatures Van Zee, Nathan J.; Coates, Geoffrey W. Angewandte Chemie International Edition, Vol. 54, Issue 9 https://doi.org/10.1002/anie.201410641	journal	January 2015
A Facile Solid-Phase Route to Renewable Aromatic Chemicals from Biobased Furanics Thiyagarajan, Shanmugam; Genuino, Homer C.; van der Waal, Jan C. Angewandte Chemie International Edition, Vol. 55, Issue 4 https://doi.org/10.1002/anie.201509346	journal	December 2015
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra ChemInform, Vol. 38, Issue 36 https://doi.org/10.1002/chin.200736263	journal	September 2007
Furfural-A Promising Platform for Lignocellulosic Biofuels Lange, Jean-Paul; van der Heide, Evert; van Buijtenen, Jeroen ChemSusChem, Vol. 5, Issue 1 https://doi.org/10.1002/cssc.201100648	journal	December 2011
Substituted Phthalic Anhydrides from Biobased Furanics: A New Approach to Renewable Aromatics Thiyagarajan, Shanmugam; Genuino, Homer C.; Śliwa, Michał ChemSusChem, Vol. 8, Issue 18 https://doi.org/10.1002/cssc.201500511	journal	July 2015
A density functional study of the simplest hydrogen abstraction reaction. Effect of self-interaction correction Johnson, Benny G.; Gonzales, Carlos A.; Gill, Peter M. W. Chemical Physics Letters, Vol. 221, Issue 1-2 https://doi.org/10.1016/0009-2614(94)87024-1	journal	April 1994
Program system for analysing positron lifetime spectra and angular correlation curves Kirkegaard, Peter; Eldrup, Morten; Mogensen, Ole E. Computer Physics Communications, Vol. 23, Issue 3 https://doi.org/10.1016/0010-4655(81)90006-0	journal	July 1981
Structure and function of a novel antioxidant peptide from the skin of tropical frogs Barbosa, Eder Alves; Oliveira, Ana; Plácido, Alexandra Free Radical Biology and Medicine, Vol. 115 https://doi.org/10.1016/j.freeradbiomed.2017.11.001	journal	February 2018
Free volume in poly(n-alkyl methacrylate)s from positron lifetime and PVT experiments and its relation to the structural relaxation Kilburn, D.; Dlubek, G.; Pionteck, J. Polymer, Vol. 47, Issue 22 https://doi.org/10.1016/j.polymer.2006.08.055	journal	October 2006
A quantum mechanical study on polymer flexibility: Extended model from monomer to tetramer of 2- and 4-bromostyrenes Navarro, Amparo; Fernández-Liencres, M. Paz; Peña-Ruiz, Tomás Polymer, Vol. 50, Issue 1 https://doi.org/10.1016/j.polymer.2008.10.041	journal	January 2009
Stereochemistry of polypeptide chain configurations Ramachandran, G. N.; Ramakrishnan, C.; Sasisekharan, V. Journal of Molecular Biology, Vol. 7, Issue 1 https://doi.org/10.1016/s0022-2836(63)80023-6	journal	July 1963
Stereochemistry of reaction paths at carbonyl centres B:urgi, H. B.; Dunitz, J. D.; Lehn, J. M. Tetrahedron, Vol. 30, Issue 12 https://doi.org/10.1016/s0040-4020(01)90678-7	journal	January 1974
Dispersion-Corrected Mean-Field Electronic Structure Methods Grimme, Stefan; Hansen, Andreas; Brandenburg, Jan Gerit Chemical Reviews, Vol. 116, Issue 9 https://doi.org/10.1021/acs.chemrev.5b00533	journal	April 2016
First-Principles Models for van der Waals Interactions in Molecules and Materials: Concepts, Theory, and Applications Hermann, Jan; DiStasio, Robert A.; Tkatchenko, Alexandre Chemical Reviews, Vol. 117, Issue 6 https://doi.org/10.1021/acs.chemrev.6b00446	journal	March 2017
Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides with Discrete Metal Complexes: Structure–Property Relationships Longo, Julie M.; Sanford, Maria J.; Coates, Geoffrey W. Chemical Reviews, Vol. 116, Issue 24 https://doi.org/10.1021/acs.chemrev.6b00553	journal	December 2016
Psi4 1.1: An Open-Source Electronic Structure Program Emphasizing Automation, Advanced Libraries, and Interoperability Parrish, Robert M.; Burns, Lori A.; Smith, Daniel G. A. Journal of Chemical Theory and Computation, Vol. 13, Issue 7 https://doi.org/10.1021/acs.jctc.7b00174	journal	June 2017
Assessing DFT-D3 Damping Functions Across Widely Used Density Functionals: Can We Do Better? Witte, Jonathon; Mardirossian, Narbe; Neaton, Jeffrey B. Journal of Chemical Theory and Computation, Vol. 13, Issue 5 https://doi.org/10.1021/acs.jctc.7b00176	journal	April 2017
Polymer Free Volume and Its Connection to the Glass Transition White, Ronald P.; Lipson, Jane E. G. Macromolecules, Vol. 49, Issue 11 https://doi.org/10.1021/acs.macromol.6b00215	journal	May 2016
Semiaromatic Polyesters Derived from Renewable Terpene Oxides with High Glass Transitions Peña Carrodeguas, Leticia; Martín, Carmen; Kleij, Arjan W. Macromolecules, Vol. 50, Issue 14 https://doi.org/10.1021/acs.macromol.7b00862	journal	July 2017
Systematic Computational and Experimental Investigation of Lithium-Ion Transport Mechanisms in Polyester-Based Polymer Electrolytes Webb, Michael A.; Jung, Yukyung; Pesko, Danielle M. ACS Central Science, Vol. 1, Issue 4 https://doi.org/10.1021/acscentsci.5b00195	journal	July 2015
Aliphatic Polyester Block Polymers: Renewable, Degradable, and Sustainable Hillmyer, Marc A.; Tolman, William B. Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500121d	journal	May 2014
Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources van Putten, Robert-Jan; van der Waal, Jan C.; de Jong, Ed Chemical Reviews, Vol. 113, Issue 3 https://doi.org/10.1021/cr300182k	journal	February 2013
Chemical Assignment of Symmetry-Adapted Perturbation Theory Interaction Energy Components: The Functional-Group SAPT Partition Parrish, Robert M.; Parker, Trent M.; Sherrill, C. David Journal of Chemical Theory and Computation, Vol. 10, Issue 10 https://doi.org/10.1021/ct500724p	journal	September 2014
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
A Preliminary Survey of the Peptoid Folding Landscape Butterfoss, Glenn L.; Renfrew, P. Douglas; Kuhlman, Brian Journal of the American Chemical Society, Vol. 131, Issue 46 https://doi.org/10.1021/ja905267k	journal	November 2009
Asymmetric Alternating Copolymerization of Meso-epoxides and Cyclic Anhydrides: Efficient Access to Enantiopure Polyesters Li, Jie; Liu, Ye; Ren, Wei-Min Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b07520	journal	August 2016
Substituent Effects on the Reversibility of Furan–Maleimide Cycloadditions Boutelle, Robert C.; Northrop, Brian H. The Journal of Organic Chemistry, Vol. 76, Issue 19 https://doi.org/10.1021/jo201606z	journal	October 2011
Ab initio studies on the structure, conformation, and chain flexibility of halogenated poly(thionylphosphazenes) Jaeger, R.; Lagowski, J. B.; Manners, I. Macromolecules, Vol. 28, Issue 2 https://doi.org/10.1021/ma00106a019	journal	March 1995
Alternating Ring-Opening Polymerization of Cyclohexene Oxide and Anhydrides: Effect of Catalyst, Cocatalyst, and Anhydride Structure Hosseini Nejad, Elham; van Melis, Carlo G. W.; Vermeer, Tim J. Macromolecules, Vol. 45, Issue 4 https://doi.org/10.1021/ma2025804	journal	February 2012
Kinetic Studies of the Alternating Copolymerization of Cyclic Acid Anhydrides and Epoxides, and the Terpolymerization of Cyclic Acid Anhydrides, Epoxides, and CO ₂ Catalyzed by (salen)Cr ^III Cl Darensbourg, Donald J.; Poland, Ross R.; Escobedo, Christina Macromolecules, Vol. 45, Issue 5 https://doi.org/10.1021/ma2026385	journal	February 2012
Sustainable polymers from renewable resources Zhu, Yunqing; Romain, Charles; Williams, Charlotte K. Nature, Vol. 540, Issue 7633 https://doi.org/10.1038/nature21001	journal	December 2016
Free volume and intrinsic microporosity in polymers Budd, Peter M.; McKeown, Neil B.; Fritsch, Detlev Journal of Materials Chemistry, Vol. 15, Issue 20 https://doi.org/10.1039/b417402j	journal	January 2005
Positronium Annihilation in Molecular Substances Tao, S. J. The Journal of Chemical Physics, Vol. 56, Issue 11 https://doi.org/10.1063/1.1677067	journal	June 1972
Segmental Mobility of Polymers Near Their Glass Temperature Bueche, F. The Journal of Chemical Physics, Vol. 21, Issue 10 https://doi.org/10.1063/1.1698677	journal	October 1953
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Glass transition and chain flexibility of linear polymers Privalko, V. P.; Lipatov, Yu. S. Journal of Macromolecular Science, Part B, Vol. 9, Issue 3 https://doi.org/10.1080/00222347408204554	journal	April 1974
Advances in molecular quantum chemistry contained in the Q-Chem 4 program package Shao, Yihan; Gan, Zhengting; Epifanovsky, Evgeny Molecular Physics, Vol. 113, Issue 2 https://doi.org/10.1080/00268976.2014.952696	journal	September 2014
The promise of plastics from plants Hillmyer, Marc A. Science, Vol. 358, Issue 6365 https://doi.org/10.1126/science.aao6711	journal	November 2017
A Theorem on Boolean Matrices Warshall, Stephen Journal of the ACM, Vol. 9, Issue 1 https://doi.org/10.1145/321105.321107	journal	January 1962
Algorithm 97: Shortest path Floyd, Robert W. Communications of the ACM, Vol. 5, Issue 6 https://doi.org/10.1145/367766.368168	journal	June 1962
Materials Science of Membranes for Gas and Vapor Separation Yampolskii, Yuri; Pinnau, Ingo; Freeman, Benny https://doi.org/10.1002/047002903X	book	June 2006
Principles of Polymerization Odian, George https://doi.org/10.1002/047147875X	book	January 2004
Principles of Polymerization Odian, George https://doi.org/10.1002/047147875x	book	January 2004
Alternating Copolymerization of Propylene Oxide with Biorenewable Terpene-Based Cyclic Anhydrides: A Sustainable Route to Aliphatic Polyesters with High Glass Transition Temperatures Van Zee, Nathan J.; Coates, Geoffrey W. Angewandte Chemie, Vol. 127, Issue 9 https://doi.org/10.1002/ange.201410641	journal	January 2015
A Facile Solid-Phase Route to Renewable Aromatic Chemicals from Biobased Furanics Thiyagarajan, Shanmugam; Genuino, Homer C.; van der Waal, Jan C. Angewandte Chemie, Vol. 128, Issue 4 https://doi.org/10.1002/ange.201509346	journal	December 2015
Alternating Copolymerization of Propylene Oxide with Biorenewable Terpene-Based Cyclic Anhydrides: A Sustainable Route to Aliphatic Polyesters with High Glass Transition Temperatures Van Zee, Nathan J.; Coates, Geoffrey W. Angewandte Chemie International Edition, Vol. 54, Issue 9 https://doi.org/10.1002/anie.201410641	journal	January 2015
A Facile Solid-Phase Route to Renewable Aromatic Chemicals from Biobased Furanics Thiyagarajan, Shanmugam; Genuino, Homer C.; van der Waal, Jan C. Angewandte Chemie International Edition, Vol. 55, Issue 4 https://doi.org/10.1002/anie.201509346	journal	December 2015
Dependence of glass transition temperature on chain flexibility and intermolecular interactions in polymers Chee, K. K. Journal of Applied Polymer Science, Vol. 43, Issue 6 https://doi.org/10.1002/app.1991.070430622	journal	September 1991
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra ChemInform, Vol. 38, Issue 36 https://doi.org/10.1002/chin.200736263	journal	September 2007
Furfural-A Promising Platform for Lignocellulosic Biofuels Lange, Jean-Paul; van der Heide, Evert; van Buijtenen, Jeroen ChemSusChem, Vol. 5, Issue 1 https://doi.org/10.1002/cssc.201100648	journal	December 2011
Substituted Phthalic Anhydrides from Biobased Furanics: A New Approach to Renewable Aromatics Thiyagarajan, Shanmugam; Genuino, Homer C.; Śliwa, Michał ChemSusChem, Vol. 8, Issue 18 https://doi.org/10.1002/cssc.201500511	journal	July 2015
Effect of chemical structure on the softening point of substituted polystyrenes and related materials Barb, W. G. Journal of Polymer Science, Vol. 37, Issue 132 https://doi.org/10.1002/pol.1959.1203713220	journal	June 1959
Free volume, glass transition, and degree of branching in metallocene-based propylene/?-olefin copolymers: Positron lifetime, density, and differential scanning calorimetric studies Dlubek, G.; Bamford, D.; Rodriguez-Gonzalez, A. Journal of Polymer Science Part B: Polymer Physics, Vol. 40, Issue 5 https://doi.org/10.1002/polb.10108	journal	January 2002
Principles of Polymerization Elias, Hans-Georg Macromolecules https://doi.org/10.1007/978-1-4615-7364-7_16	book	January 1977
A density functional study of the simplest hydrogen abstraction reaction. Effect of self-interaction correction Johnson, Benny G.; Gonzales, Carlos A.; Gill, Peter M. W. Chemical Physics Letters, Vol. 221, Issue 1-2 https://doi.org/10.1016/0009-2614(94)87024-1	journal	April 1994
Program system for analysing positron lifetime spectra and angular correlation curves Kirkegaard, Peter; Eldrup, Morten; Mogensen, Ole E. Computer Physics Communications, Vol. 23, Issue 3 https://doi.org/10.1016/0010-4655(81)90006-0	journal	July 1981
An infra-red study of conformational changes occurring during the drawing of PEMT, PET and PEMT/PET copolymer Spiby, P.; Oneill, M.; Duckett, R. Polymer, Vol. 33, Issue 21 https://doi.org/10.1016/0032-3861(92)90403-J	journal	January 1992
Principles of polymerization Peppas, N. A. Journal of Controlled Release, Vol. 22, Issue 3 https://doi.org/10.1016/0168-3659(92)90108-4	journal	November 1992
Cooperative molecular dynamics and strong/fragile behavior of polymers Solunov, Christo Alexandrov European Polymer Journal, Vol. 35, Issue 8 https://doi.org/10.1016/S0014-3057(98)00226-2	journal	August 1999
Stereochemistry of polypeptide chain configurations Ramachandran, G. N.; Ramakrishnan, C.; Sasisekharan, V. Journal of Molecular Biology, Vol. 7, Issue 1 https://doi.org/10.1016/S0022-2836(63)80023-6	journal	July 1963
Stereochemistry of reaction paths at carbonyl centres B:urgi, H. B.; Dunitz, J. D.; Lehn, J. M. Tetrahedron, Vol. 30, Issue 12 https://doi.org/10.1016/S0040-4020(01)90678-7	journal	January 1974
Internal rotation barriers: ab initio calculations on substituted ethyl benzoates and benzoic acids as models for polyester flexibility Nelson, Michael R.; Borkman, Raymond F. Journal of Molecular Structure: THEOCHEM, Vol. 432, Issue 3 https://doi.org/10.1016/S0166-1280(98)00080-3	journal	June 1998
Free volume in poly(n-alkyl methacrylate)s from positron lifetime and PVT experiments and its relation to the structural relaxation Kilburn, D.; Dlubek, G.; Pionteck, J. Polymer, Vol. 47, Issue 22 https://doi.org/10.1016/j.polymer.2006.08.055	journal	October 2006
A quantum mechanical study on polymer flexibility: Extended model from monomer to tetramer of 2- and 4-bromostyrenes Navarro, Amparo; Fernández-Liencres, M. Paz; Peña-Ruiz, Tomás Polymer, Vol. 50, Issue 1 https://doi.org/10.1016/j.polymer.2008.10.041	journal	January 2009
Program system for analysing positron lifetime spectra and angular correlation curves Kirkegaard, Peter; Eldrup, Morten; Mogensen, Ole E. Computer Physics Communications, Vol. 35 https://doi.org/10.1016/s0010-4655(84)82867-2	journal	January 1984
Dispersion-Corrected Mean-Field Electronic Structure Methods Grimme, Stefan; Hansen, Andreas; Brandenburg, Jan Gerit Chemical Reviews, Vol. 116, Issue 9 https://doi.org/10.1021/acs.chemrev.5b00533	journal	April 2016
First-Principles Models for van der Waals Interactions in Molecules and Materials: Concepts, Theory, and Applications Hermann, Jan; DiStasio, Robert A.; Tkatchenko, Alexandre Chemical Reviews, Vol. 117, Issue 6 https://doi.org/10.1021/acs.chemrev.6b00446	journal	March 2017
Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides with Discrete Metal Complexes: Structure–Property Relationships Longo, Julie M.; Sanford, Maria J.; Coates, Geoffrey W. Chemical Reviews, Vol. 116, Issue 24 https://doi.org/10.1021/acs.chemrev.6b00553	journal	December 2016
Psi4 1.1: An Open-Source Electronic Structure Program Emphasizing Automation, Advanced Libraries, and Interoperability Parrish, Robert M.; Burns, Lori A.; Smith, Daniel G. A. Journal of Chemical Theory and Computation, Vol. 13, Issue 7 https://doi.org/10.1021/acs.jctc.7b00174	journal	June 2017
Assessing DFT-D3 Damping Functions Across Widely Used Density Functionals: Can We Do Better? Witte, Jonathon; Mardirossian, Narbe; Neaton, Jeffrey B. Journal of Chemical Theory and Computation, Vol. 13, Issue 5 https://doi.org/10.1021/acs.jctc.7b00176	journal	April 2017
Polymer Free Volume and Its Connection to the Glass Transition White, Ronald P.; Lipson, Jane E. G. Macromolecules, Vol. 49, Issue 11 https://doi.org/10.1021/acs.macromol.6b00215	journal	May 2016
Alternating Copolymerization of Propylene Oxide and Cyclohexene Oxide with Tricyclic Anhydrides: Access to Partially Renewable Aliphatic Polyesters with High Glass Transition Temperatures Sanford, Maria J.; Peña Carrodeguas, Leticia; Van Zee, Nathan J. Macromolecules, Vol. 49, Issue 17 https://doi.org/10.1021/acs.macromol.6b01425	journal	August 2016
Semiaromatic Polyesters Derived from Renewable Terpene Oxides with High Glass Transitions Peña Carrodeguas, Leticia; Martín, Carmen; Kleij, Arjan W. Macromolecules, Vol. 50, Issue 14 https://doi.org/10.1021/acs.macromol.7b00862	journal	July 2017
Systematic Computational and Experimental Investigation of Lithium-Ion Transport Mechanisms in Polyester-Based Polymer Electrolytes Webb, Michael A.; Jung, Yukyung; Pesko, Danielle M. ACS Central Science, Vol. 1, Issue 4 https://doi.org/10.1021/acscentsci.5b00195	journal	July 2015
Free Volume in the Melt and How It Correlates with Experimental Glass Transition Temperatures: Results for a Large Set of Polymers White, Ronald P.; Lipson, Jane E. G. ACS Macro Letters, Vol. 4, Issue 5 https://doi.org/10.1021/acsmacrolett.5b00217	journal	April 2015
Aliphatic Polyester Block Polymers: Renewable, Degradable, and Sustainable Hillmyer, Marc A.; Tolman, William B. Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500121d	journal	May 2014
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502 https://doi.org/10.1021/cr050989d	journal	June 2007
Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources van Putten, Robert-Jan; van der Waal, Jan C.; de Jong, Ed Chemical Reviews, Vol. 113, Issue 3 https://doi.org/10.1021/cr300182k	journal	February 2013
Chemical Assignment of Symmetry-Adapted Perturbation Theory Interaction Energy Components: The Functional-Group SAPT Partition Parrish, Robert M.; Parker, Trent M.; Sherrill, C. David Journal of Chemical Theory and Computation, Vol. 10, Issue 10 https://doi.org/10.1021/ct500724p	journal	September 2014
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
A Preliminary Survey of the Peptoid Folding Landscape Butterfoss, Glenn L.; Renfrew, P. Douglas; Kuhlman, Brian Journal of the American Chemical Society, Vol. 131, Issue 46 https://doi.org/10.1021/ja905267k	journal	November 2009
Electronic Effects of Aluminum Complexes in the Copolymerization of Propylene Oxide with Tricyclic Anhydrides: Access to Well-Defined, Functionalizable Aliphatic Polyesters Van Zee, Nathan J.; Sanford, Maria J.; Coates, Geoffrey W. Journal of the American Chemical Society, Vol. 138, Issue 8 https://doi.org/10.1021/jacs.5b12888	journal	February 2016
Asymmetric Alternating Copolymerization of Meso-epoxides and Cyclic Anhydrides: Efficient Access to Enantiopure Polyesters Li, Jie; Liu, Ye; Ren, Wei-Min Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b07520	journal	August 2016
Substituent Effects on the Reversibility of Furan–Maleimide Cycloadditions Boutelle, Robert C.; Northrop, Brian H. The Journal of Organic Chemistry, Vol. 76, Issue 19 https://doi.org/10.1021/jo201606z	journal	October 2011
Ab initio studies on the structure, conformation, and chain flexibility of halogenated poly(thionylphosphazenes) Jaeger, R.; Lagowski, J. B.; Manners, I. Macromolecules, Vol. 28, Issue 2 https://doi.org/10.1021/ma00106a019	journal	March 1995
Addition-Type Polynorbornenes with Si(CH₃)₃ Side Groups: Synthesis, Gas Permeability, and Free Volume Finkelshtein, E. Sh.; Makovetskii, K. L.; Gringolts, M. L. Macromolecules, Vol. 39, Issue 20, p. 7022-7029 https://doi.org/10.1021/ma061215h	journal	October 2006
Alternating Ring-Opening Polymerization of Cyclohexene Oxide and Anhydrides: Effect of Catalyst, Cocatalyst, and Anhydride Structure Hosseini Nejad, Elham; van Melis, Carlo G. W.; Vermeer, Tim J. Macromolecules, Vol. 45, Issue 4 https://doi.org/10.1021/ma2025804	journal	February 2012
Kinetic Studies of the Alternating Copolymerization of Cyclic Acid Anhydrides and Epoxides, and the Terpolymerization of Cyclic Acid Anhydrides, Epoxides, and CO ₂ Catalyzed by (salen)Cr ^III Cl Darensbourg, Donald J.; Poland, Ross R.; Escobedo, Christina Macromolecules, Vol. 45, Issue 5 https://doi.org/10.1021/ma2026385	journal	February 2012
Sustainable polymers from renewable resources Zhu, Yunqing; Romain, Charles; Williams, Charlotte K. Nature, Vol. 540, Issue 7633 https://doi.org/10.1038/nature21001	journal	December 2016
Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride Mahmoud, Eyas; Watson, Donald A.; Lobo, Raul F. Green Chem., Vol. 16, Issue 1 https://doi.org/10.1039/C3GC41655K	journal	January 2014
Ring-opening copolymerization (ROCOP): synthesis and properties of polyesters and polycarbonates Paul, Shyeni; Zhu, Yunqing; Romain, Charles Chemical Communications, Vol. 51, Issue 30 https://doi.org/10.1039/C4CC10113H	journal	January 2015
Di-magnesium and zinc catalysts for the copolymerization of phthalic anhydride and cyclohexene oxide Saini, Prabhjot K.; Romain, Charles; Zhu, Yunqing Polym. Chem., Vol. 5, Issue 20 https://doi.org/10.1039/C4PY00748D	journal	January 2014
Free volume and intrinsic microporosity in polymers Budd, Peter M.; McKeown, Neil B.; Fritsch, Detlev Journal of Materials Chemistry, Vol. 15, Issue 20 https://doi.org/10.1039/b417402j	journal	January 2005
Positronium Annihilation in Molecular Substances Tao, S. J. The Journal of Chemical Physics, Vol. 56, Issue 11 https://doi.org/10.1063/1.1677067	journal	June 1972
Segmental Mobility of Polymers Near Their Glass Temperature Bueche, F. The Journal of Chemical Physics, Vol. 21, Issue 10 https://doi.org/10.1063/1.1698677	journal	October 1953
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Communication: Practical intramolecular symmetry adapted perturbation theory via Hartree-Fock embedding Parrish, Robert M.; Gonthier, Jérôme F.; Corminbœuf, Clémence The Journal of Chemical Physics, Vol. 143, Issue 5 https://doi.org/10.1063/1.4927575	journal	August 2015
Intramolecular symmetry-adapted perturbation theory with a single-determinant wavefunction Pastorczak, Ewa; Prlj, Antonio; Gonthier, Jérôme F. The Journal of Chemical Physics, Vol. 143, Issue 22 https://doi.org/10.1063/1.4936830	journal	December 2015
Glass transition and chain flexibility of linear polymers Privalko, V. P.; Lipatov, Yu. S. Journal of Macromolecular Science, Part B, Vol. 9, Issue 3 https://doi.org/10.1080/00222347408204554	journal	April 1974
Advances in molecular quantum chemistry contained in the Q-Chem 4 program package Shao, Yihan; Gan, Zhengting; Epifanovsky, Evgeny Molecular Physics, Vol. 113, Issue 2 https://doi.org/10.1080/00268976.2014.952696	journal	September 2014
Self-interaction correction to density-functional approximations for many-electron systems Perdew, J. P.; Zunger, Alex Physical Review B, Vol. 23, Issue 10, p. 5048-5079 https://doi.org/10.1103/PhysRevB.23.5048	journal	May 1981
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
The promise of plastics from plants Hillmyer, Marc A. Science, Vol. 358, Issue 6365 https://doi.org/10.1126/science.aao6711	journal	November 2017
A Theorem on Boolean Matrices Warshall, Stephen Journal of the ACM, Vol. 9, Issue 1 https://doi.org/10.1145/321105.321107	journal	January 1962
Algorithm 97: Shortest path Floyd, Robert W. Communications of the ACM, Vol. 5, Issue 6 https://doi.org/10.1145/367766.368168	journal	June 1962
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Robert, Parr,; Chengteh, Lee,; Weitao, Yang, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/zrp0-ry04	text	January 1988

Cited By (2)

Easy access to oxygenated block polymers via switchable catalysis Stößer, Tim; Sulley, Gregory S.; Gregory, Georgina L. Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10481-w	journal	June 2019
Easy access to oxygenated block polymers via switchable catalysis Stößer, Tim; Sulley, Gregory S.; Gregory, Georgina L. Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10481-w	journal	June 2019

Similar Records

Enhancing Biopolyester Backbone Rigidity with an Asymmetric Furanic Monomer

Journal Article · 2025 · ACS Sustainable Chemistry & Engineering · OSTI ID:3000213

Woroch, Cristian P.; Addison, Bennett; Stovall, Alexandra; +7 more

Biorenewable and circular polydiketoenamine plastics

Journal Article · 2023 · Nature Sustainability · OSTI ID:2248088

Demarteau, Jeremy; Cousineau, Benjamin; Wang, Zilong; +8 more

Unraveling the Mechanism of Nanoscale Mechanical Reinforcement in Glassy Polymer Nanocomposites

Journal Article · 2016 · Nano Letters · OSTI ID:1271894

Cheng, Shiwang; Bocharova, Vera; Belianinov, Alex; +10 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Other Topics
Science & Technology

Title: Unraveling substituent effects on the glass transition temperatures of biorenewable polyesters

Citation Formats

References (107)

Cited By (2)

Similar Records

Related Subjects