Covalent Adaptable Networks (CANs): A Unique Paradigm in Cross-Linked Polymers
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Polymer networks possessing reversible covalent crosslinks constitute a novel material class with the capacity for adapting to an externally applied stimulus. These covalent adaptable networks (CANs) represent a trend in polymer network fabrication towards the rational design of structural materials possessing dynamic characteristics for specialty applications. Herein, we discuss the unique attributes of CANs that must be considered when designing, fabricating, and characterizing these smart materials that respond to either thermal or photochemical stimuli. While there are many reversible reactions which to consider as possible crosslink candidates in CANs, there are very few that are readily and repeatedly reversible. Furthermore, characterization of the mechanical properties of CANs requires special consideration owing to their unique attributes. Ultimately, these attributes are what lead to the advantageous properties displayed by CANs, such as recyclability, healability, tunability, shape changes, and low polymerization stress. Throughout this perspective, we identify several trends and future directions in the emerging field of CANs that demonstrate the progress to date as well as the essential elements that are needed for further advancement.
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Existing strategies to create reprocessable thermosets have focused on dynamic covalent bond exchange, thermomechanical degradation, or wholesale replacement of network components with degradable versions.
“Existing strategies to create reprocessable thermosets have focused on dynamic covalent bond exchange, 3-8 thermomechanical degradation, 9 or wholesale replacement of network components with degradable versions. 10-13”
From Cleavable comonomers enable degradable, recyclable thermoset plastics (2020) · cites this paper as [3]
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Cites
Principles of Polymer Chemistry.
Huggins, M. L. (1954) · Journal of the American Chemical Society · doi:10.1021/ja01639a090 · Cited by 16,657 · see citing works
Scaling concepts in polymer physics
Gordon, M. (1981) · Polymer · doi:10.1016/0032-3861(81)90183-x · Cited by 10,559 · see citing works
Autonomic healing of polymer composites
White, S. R., Sottos, N. R., Geubelle, P. H., Moore, J. S., Kessler, M. R., Sriram, S. R., Brown, E. N., & Viswanathan, S. (2001) · Nature · doi:10.1038/35057232 · Cited by 4,575 · see citing works
Brabec, C. J., Sariçiftçi, N. S., & Hummelen, J. C. (2001) · Advanced Functional Materials · doi:10.1002/1616-3028(200102)11:1 · Cited by 3,836 · see citing works
A Thermally Re-mendable Cross-Linked Polymeric Material
Chen, X., Dam, M. A., Ono, K., Mal, A., Shen, H., Nutt, S., Sheran, K., & Wudl, F. (2002) · Science · doi:10.1126/science.1065879 · Cited by 2,649 · see citing works
Rowan, S. J., Cantrill, S., Cousins, G. R. L., Sanders, J. K. M., & Stoddart, J. F. (2002) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20020315)41:6 · Cited by 2,599 · see citing works
Analysis of Linear Viscoelasticity of a Crosslinking Polymer at the Gel Point
Winter, H. H., & Chambon, F. (1986) · Journal of Rheology · doi:10.1122/1.549853 · Cited by 2,466 · see citing works
Light-induced shape-memory polymers
Lendlein, A., Jiang, H., Jünger, O., & Langer, R. (2005) · Nature · doi:10.1038/nature03496 · Cited by 2,006 · see citing works
Molecular Size Distribution in Three Dimensional Polymers. I. Gelation 1
Flory, P. J. (1941) · Journal of the American Chemical Society · doi:10.1021/ja01856a061 · Cited by 1,924 · see citing works
Theory of Molecular Size Distribution and Gel Formation in Branched-Chain Polymers
STOCKMAYER, W. H. (1943) · The Journal of Chemical Physics · doi:10.1063/1.1723803 · Cited by 1,919 · see citing works
Ruhland, K. (2020) · Catalysis from A to Z · doi:10.1002/9783527809080.cataz06077 · Cited by 1,727 · see citing works
Linear Viscoelasticity at the Gel Point of a Crosslinking PDMS with Imbalanced Stoichiometry
Chambon, F., & Winter, H. H. (1987) · Journal of Rheology · doi:10.1122/1.549955 · Cited by 1,254 · see citing works
Self-healing materials: a review
Wool, R. P. (2008) · Soft Matter · doi:10.1039/b711716g · Cited by 1,033 · see citing works
Coumarins in Polymers: From Light Harvesting to Photo-Cross-Linkable Tissue Scaffolds
Trenor, S. R., Shultz, A. R., Love, B. J., & Long, T. E. (2004) · Chemical Reviews · doi:10.1021/cr030037c · Cited by 791 · see citing works
Can the gel point of a cross‐linking polymer be detected by the G′ – G″ crossover?
Winter, H. H. (1987) · Polymer Engineering and Science · doi:10.1002/pen.760272209 · Cited by 786 · see citing works
Photoinduced Plasticity in Cross-Linked Polymers
Scott, T. F., Schneider, A. D., Cook, W. D., & Bowman, C. N. (2005) · Science · doi:10.1126/science.1110505 · Cited by 779 · see citing works
Self-citationPolymerization shrinkage and polymerization shrinkage stress in polymer-based restoratives
Davidson, C. L., & Feilzer, A. J. (1997) · Journal of Dentistry · doi:10.1016/s0300-5712(96)00063-2 · Cited by 731 · see citing works
New Thermally Remendable Highly Cross-Linked Polymeric Materials
Chen, X., Wudl, F., Mal, A., Shen, H., & Nutt, S. (2003) · Macromolecules · doi:10.1021/ma0210675 · Cited by 703 · see citing works
Bergman, S. D., & Wudl, F. (2007) · Journal of Materials Chemistry · doi:10.1039/b713953p · Cited by 652 · see citing works
Polymers move in response to light
Jiang, H. Y., Kelch, S., & Lendlein, A. (2006) · Advanced Materials · doi:10.1002/adma.200502266 · Cited by 631 · see citing works
Polymerization shrinkage and elasticity of flowable composites and filled adhesives
Labella, R., Lambrechts, P., MEERBEEK, B. V., et al. (1999) · Dental Materials · doi:10.1016/s0109-5641(99)00022-6 · Cited by 599 · see citing works
Thermally Self-Healing Polymeric Materials: The Next Step to Recycling Thermoset Polymers?
Zhang, Y., Broekhuis, A. A., & Picchioni, F. (2009) · Macromolecules · doi:10.1021/ma8027672 · Cited by 476 · see citing works
Stopping of crosslinking reaction in a PDMS polymer at the gel point
Chambon, F., & Winter, H. H. (1985) · Polymer Bulletin · doi:10.1007/bf00263470 · Cited by 448 · see citing works
Crack Healing in Polymeric Materials via Photochemical [2+2] Cycloaddition
Chung, C., Roh, Y.-S., Cho, S., & Kim, J. (2004) · Chemistry of Materials · doi:10.1021/cm049394+ · Cited by 402 · see citing works
Screening effect on viscoelasticity near the gel point
Muthukumar, M. (1989) · Macromolecules · doi:10.1021/ma00202a050 · Cited by 393 · see citing works
The Diels-Alder Reaction Selected Practical Methods
Connon, S. J. (2002) · Synthesis · doi:10.1055/s-2002-25752 · Cited by 388 · see citing works
Cell adaptation to a physiologically relevant ECM mimic with different viscoelastic properties
Ghosh, K., Pan, Z., Guan, E., Ge, S., Liu, Y., Nakamura, T., Ren, X.-D., Rafailovich, M., & Clark, R. A. F. (2007) · Biomaterials · doi:10.1016/j.biomaterials.2006.09.038 · Cited by 386 · see citing works
Hybrid polymer/sol–gel waveguide modulators with exceptionally large electro–optic coefficients
Enami, Y., Derose, C. T., Mathine, D., Loychik, C., Greenlee, C., Norwood, R. A., Kim, T. D., Luo, J., Tian, Y., Jen, A. K.-Y., et al. (2007) · Nature Photonics · doi:10.1038/nphoton.2007.25 · Cited by 355 · see citing works
Adzima, B. J., Aguirre‐Soto, A., Kloxin, C. J., Scott, T. F., & Bowman, C. N. (2008) · Macromolecules · doi:10.1021/ma801863d · Cited by 355 · see citing works
Self-citationSkene, W. G., & Lehn, J.-M. P. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0401885101 · Cited by 348 · see citing works
Gheneim, R., Perez-Berumen, C. M., & Gandini, A. (2002) · Macromolecules · doi:10.1021/ma020343c · Cited by 294 · see citing works
Room Temperature Dynamic Polymers Based on Diels–Alder Chemistry
Reutenauer, P., Buhler, E., Boul, P. J., Candau, S. J., & Lehn, J. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200802145 · Cited by 291 · see citing works
Toward an enhanced understanding and implementation of photopolymerization reactions
Bowman, C. N., & Kloxin, C. J. (2008) · AIChE Journal · doi:10.1002/aic.11678 · Cited by 281 · see citing works
Self-citationInvestigations of step-growth thiol-ene polymerizations for novel dental restoratives
Lu, H. Z., Carioscia, J. A., Stansbury, J. W., & Bowman, C. N. (2005) · Dental Materials · doi:10.1016/j.dental.2005.04.001 · Cited by 269 · see citing works
Self-citationLiu, Y., & Hsieh, C. (2005) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21184 · Cited by 267 · see citing works
A thermally remendable epoxy resin
Tian, Q., Yuan, Y., Rong, M. Z., & Zhang, M. Q. (2009) · Journal of Materials Chemistry · doi:10.1039/b811938d · Cited by 257 · see citing works
Bryant, S. J., Chowdhury, T. T., Lee, D. A., Bader, D. L., & Anseth, K. S. (2004) · Annals of Biomedical Engineering · doi:10.1023/b:abme.0000017535.00602.ca · Cited by 242 · see citing works
Stress Relaxation of Natural and Synthetic Rubber Stocks
Tobolsky, A. V., Prettyman, I. B., & Dillon, J. H. (1944) · Journal of Applied Physics · doi:10.1063/1.1707442 · Cited by 238 · see citing works
Liu, Y., & Chen, Y. (2007) · Macromolecular Chemistry and Physics · doi:10.1002/macp.200600445 · Cited by 236 · see citing works
Goussé, C., Gandini, A., & Hodge, P. (1998) · Macromolecules · doi:10.1021/ma9710141 · Cited by 226 · see citing works
Murphy, E. B., Bolanos, E., Schaffner-Hamann, C., et al. (2008) · Macromolecules · doi:10.1021/ma800432g · Cited by 209 · see citing works
The Theory of Permanent Set at Elevated Temperatures in Natural and Synthetic Rubber Vulcanizates
Andrews, R. D., Tobolsky, A. V., & Hanson, E. E. (1946) · Journal of Applied Physics · doi:10.1063/1.1707724 · Cited by 199 · see citing works
Islangulov, R. R., & Castellano, F. N. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200601615 · Cited by 193 · see citing works
Thermally Reversible IPN Organic−Inorganic Polymer Hybrids Utilizing the Diels−Alder Reaction
Imai, Y., Itoh, H., Naka, K., & Chujo, Y. (2000) · Macromolecules · doi:10.1021/ma991899b · Cited by 184 · see citing works
A Thermodynamic Polymer Cross-Linking System Based on Radically Exchangeable Covalent Bonds
Higaki, Y., Otsuka, H., & Takahara, A. (2006) · Macromolecules · doi:10.1021/ma052093g · Cited by 172 · see citing works
PEG-Based Hydrogel Synthesis via the Photodimerization of Anthracene Groups
Zheng, Y. G., Mićić, M., Mello, S. V., Mabrouki, M., Andreopoulos, F. M., Konka, V., Pham, S. M., & Leblanc, R. M. (2002) · Macromolecules · doi:10.1021/ma012263z · Cited by 172 · see citing works
Liu, Y., Hsieh, C., & Chen, Y. (2006) · Polymer · doi:10.1016/j.polymer.2006.02.057 · Cited by 169 · see citing works
Stress Relaxation via Addition−Fragmentation Chain Transfer in a Thiol-ene Photopolymerization
Kloxin, C. J., Scott, T. F., & Bowman, C. N. (2009) · Macromolecules · doi:10.1021/ma802771b · Cited by 161 · see citing works
Self-citationDynamic covalent polymers based upon carbene dimerization
Kamplain, J. W., & Bielawski, C. W. (2006) · Chemical Communications · doi:10.1039/b518246h · Cited by 157 · see citing works
Watanabe, M., & Yoshie, N. (2006) · Polymer · doi:10.1016/j.polymer.2006.05.036 · Cited by 151 · see citing works
Actuation in Crosslinked Polymers via Photoinduced Stress Relaxation
Scott, T. F., Draughon, R. B., & Bowman, C. N. (2006) · Advanced Materials · doi:10.1002/adma.200600379 · Cited by 150 · see citing works
Self-citationViscoelastic properties of physically crosslinked networks
Tanaka, F., & Edwards, S. F. (1992) · Journal of Non-Newtonian Fluid Mechanics · doi:10.1016/0377-0257(92)80028-v · Cited by 149 · see citing works
Meijs, G. F., Rizzardo, E., & Thang, S. H. (1988) · Macromolecules · doi:10.1021/ma00188a039 · Cited by 149 · see citing works
Reversible Diels−Alder Reactions for the Generation of Dynamic Combinatorial Libraries
Boul, P. J., Reutenauer, P., & Lehn, J. (2004) · Organic Letters · doi:10.1021/ol048065k · Cited by 148 · see citing works
Sensitized photodimerization of thymine in DNA.
Lamola, A. A., & Yamane, T. (1967) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.58.2.443 · Cited by 145 · see citing works
Degradable Cross-Linkers and Strippable Imaging Materials for Step-and-Flash Imprint Lithography
Heath, W. H., Palmieri, F. L., Adams, J. R., et al. (2008) · Macromolecules · doi:10.1021/ma702291k · Cited by 132 · see citing works
The effect of entanglements on the rheological behavior of polybutadiene critical gels
Rosa, M. E. D., & Winter, H. H. (1994) · Rheologica Acta · doi:10.1007/bf00437307 · Cited by 132 · see citing works
Dynamical critical behavior during chemical gelation and vulcanization
Hess, W., Vilgis, T. A., & Winter, H. H. (1988) · Macromolecules · doi:10.1021/ma00186a037 · Cited by 129 · see citing works
Laita, H., Boufi, S., & Gandini, A. (1997) · European Polymer Journal · doi:10.1016/s0014-3057(97)00009-8 · Cited by 126 · see citing works
Kim, T., Luo, J., Ka, J., Hau, Ş., Tian, Y., Shi, Z., Tucker, N. M., Jang, S. ‐., Kang, J., & Jen, A. K. ‐. (2006) · Advanced Materials · doi:10.1002/adma.200601582 · Cited by 118 · see citing works
Removable foams based on an epoxy resin incorporating reversible Diels–Alder adducts
McElhanon, J. R., Russick, E. M., Wheeler, D. R., et al. (2002) · Journal of Applied Polymer Science · doi:10.1002/app.10753 · Cited by 115 · see citing works
New Free-Radical Ring-Opening Acrylate Monomers
Evans, R. A., Moad, G., Rizzardo, E., & Thang, S. H. (1994) · Macromolecules · doi:10.1021/ma00104a062 · Cited by 112 · see citing works
Free-Radical ring-opening polymerization of cyclic allylic sulfides
Evans, R. A., & Rizzardo, E. (1996) · Macromolecules · doi:10.1021/ma960573p · Cited by 110 · see citing works
Nagata, M., & Yamamoto, Y. (2009) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.23333 · Cited by 108 · see citing works
Meijs, G. F., Morton, T. C., Rizzardo, E., & Thang, S. H. (1991) · Macromolecules · doi:10.1021/ma00012a033 · Cited by 106 · see citing works
Amamoto, Y., Higaki, Y., Matsuda, Y., Otsuka, H., & Takahara, A. (2007) · Journal of the American Chemical Society · doi:10.1021/ja075447n · Cited by 101 · see citing works
Gotsmann, B., Duerig, U. T., Frommer, J., et al. (2006) · Advanced Functional Materials · doi:10.1002/adfm.200500724 · Cited by 100 · see citing works
Fabrication of Reversibly Crosslinkable, 3‐Dimensionally Conformal Polymeric Microstructures
Connal, L. A., Vestberg, R., Hawker, C. J., et al. (2008) · Advanced Functional Materials · doi:10.1002/adfm.200800333 · Cited by 95 · see citing works
Highly Efficient Diels–Alder Crosslinkable Electro‐Optic Dendrimers for Electric‐Field Sensors
Shi, Z., Hau, S., Luo, J., et al. (2007) · Advanced Functional Materials · doi:10.1002/adfm.200600778 · Cited by 90 · see citing works
Goiti, E., Heatley, F., Huglin, M. B., et al. (2004) · European Polymer Journal · doi:10.1016/j.eurpolymj.2004.01.036 · Cited by 85 · see citing works
Kennedy, J. P., & Castner, K. F. (1979) · Journal of Polymer Science Polymer Chemistry Edition · doi:10.1002/pol.1979.170170715 · Cited by 81 · see citing works
Photoreversible poly(ethylene glycol)s with pendent coumarin group and their hydrogels
Nagata, M., & Yamamoto, Y. (2008) · Reactive and Functional Polymers · doi:10.1016/j.reactfunctpolym.2008.01.003 · Cited by 79 · see citing works
Kavitha, A. A., & Singha, N. K. (2007) · Macromolecular Chemistry and Physics · doi:10.1002/macp.200700239 · Cited by 78 · see citing works
Gattás‐Asfura, K. M., Weisman, E., Andreopoulos, F. M., et al. (2005) · Biomacromolecules · doi:10.1021/bm049238w · Cited by 76 · see citing works
Amamoto, Y., Kikuchi, M., Masunaga, H., et al. (2009) · Macromolecules · doi:10.1021/ma901746n · Cited by 74 · see citing works
Nitrogen-centered free radicals. IX. The ease of formation of thionitroxide radicals
Danen, W. C., & Newkirk, D. D. (1976) · Journal of the American Chemical Society · doi:10.1021/ja00418a031 · Cited by 73 · see citing works
Materials for step and flash imprint lithography (S-FIL®)
Long, B. K., Keitz, B. K., & Willson, C. G. (2007) · Journal of Materials Chemistry · doi:10.1039/b705388f · Cited by 67 · see citing works
Goiti, E., Huglin, M. B., & Rego, J. M. (2003) · European Polymer Journal · doi:10.1016/j.eurpolymj.2003.09.017 · Cited by 66 · see citing works
Two-way conversion between hard and soft properties of semicrystalline cross-linked polymer
Ishida, K., & Yoshie, N. (2008) · Macromolecules · doi:10.1021/ma8008383 · Cited by 66 · see citing works
A Review of Thermally Controlled Covalent Bond Formation in Polymer Chemistry
Engle, L. P., & Wagener, K. B. (1993) · Journal of macromolecular science. Part C, Reviews in macromolecular chemistry and physics/Journal of macromolecular science. Reviews in macromolecular chemistry and physics · doi:10.1080/15321799308021436 · Cited by 65 · see citing works
Goiti, E., Huglin, M. B., & Rego, J. M. (2003) · Macromolecular Rapid Communications · doi:10.1002/marc.200350013 · Cited by 59 · see citing works
Synthesis of Readily Recyclable Biobased Plastics by Diels‐Alder Reaction
Ishida, K., & Yoshie, N. (2008) · Macromolecular Bioscience · doi:10.1002/mabi.200800078 · Cited by 58 · see citing works
Maillard, B., & Ingold, K. U. (1976) · Journal of the American Chemical Society · doi:10.1021/ja00418a032 · Cited by 55 · see citing works
Evans, R. A., & Rizzardo, E. (2000) · Macromolecules · doi:10.1021/ma9917646 · Cited by 53 · see citing works
Evans, R. A., & Rizzardo, E. (2000) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/1099-0518(20010101)39:1 · Cited by 46 · see citing works
Reutenauer, P., Boul, P. J., & Lehn, J. (2009) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200801269 · Cited by 44 · see citing works
Mićić, M., Zheng, Y. G., Moy, V. T., et al. (2002) · Colloids and Surfaces B Biointerfaces · doi:10.1016/s0927-7765(02)00051-6 · Cited by 43 · see citing works
Karthikeyan, S., & Ramamurthy, V. (2005) · Tetrahedron Letters · doi:10.1016/j.tetlet.2005.04.115 · Cited by 43 · see citing works
Hartman, R. F., & Rose, S. D. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00035a063 · Cited by 42 · see citing works
Harrisson, S., Davis, T. P., Evans, R. A., & Rizzardo, E. (2001) · Macromolecules · doi:10.1021/ma0020584 · Cited by 41 · see citing works
Triplet-state sensitization of thymine photodimerization in bacteriophage T4
Meistrich, M. L., & Lamola, A. A. (1972) · Journal of Molecular Biology · doi:10.1016/s0022-2836(72)80007-x · Cited by 37 · see citing works
Ren, B., Zhao, D., Liu, S., et al. (2007) · Macromolecules · doi:10.1021/ma062502o · Cited by 35 · see citing works
van der Mee, M. A. J., Goossens, H., & van Duin, M. (2008) · Polymer · doi:10.1016/j.polymer.2008.01.031 · Cited by 35 · see citing works
Giant Molecules: Here, There, and Everywhere…
Grosberg, A. Y., Khokhlov, A. R., & Jelinski, L. W. (1997) · American Journal of Physics · doi:10.1119/1.18660 · Cited by 33 · see citing works
Harrisson, S., Davis, T. P., Evans, R. A., & Rizzardo, E. (2000) · Macromolecules · doi:10.1021/ma0010579 · Cited by 31 · see citing works
Thermally reversible polymer linkages. 3. Covalently crosslinked poly(azlactone)
Wagener, K. B., & Engle, L. P. (1991) · Macromolecules · doi:10.1021/ma00026a001 · Cited by 30 · see citing works
Matsui, J., Ochi, Y., & Tamaki, K. (2005) · Chemistry Letters · doi:10.1246/cl.2006.80 · Cited by 30 · see citing works
Zhao, D., Ren, B., Liu, S., et al. (2006) · Chemical Communications · doi:10.1039/b515413h · Cited by 30 · see citing works
A sol–gel reaction of vinyl polymers based on thermally reversible urea linkages
Chang, J. Y., Ku, S., & Han, M. J. (2001) · Polymer · doi:10.1016/s0032-3861(01)00270-1 · Cited by 28 · see citing works
Thermoreversible covalent crosslinking of maleated ethylene/propylene copolymers with diols
van der Mee, M. A. J., Goossens, H., & van Duin, M. (2008) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.22524 · Cited by 27 · see citing works
Photosensitized monomerization of 1,3-dimethyluracil photodimers
Sasson, S., & Elad, D. (1972) · The Journal of Organic Chemistry · doi:10.1021/jo00985a027 · Cited by 21 · see citing works
Ermoshkin, A. A., Neckers, D. C., & Fedorov, A. V. (2006) · Macromolecules · doi:10.1021/ma060905i · Cited by 20 · see citing works
Allene Chemistry. IV. Unsymmetrical Terminal Thiol—Allene Diadducts. The Effect of Allylic Reversal1
Hall, D. N., Oswald, A. A., & Griesbaum, K. (1965) · The Journal of Organic Chemistry · doi:10.1021/jo01022a054 · Cited by 19 · see citing works
Harrisson, S., Davis, T. P., Evans, R. A., & Rizzardo, E. (2002) · Macromolecules · doi:10.1021/ma0111663 · Cited by 19 · see citing works
Chavigny, C., Bideau, F. L., Pradier, C., et al. (1998) · Chemical Communications · doi:10.1039/a802551g · Cited by 18 · see citing works
Formation of IPN organic-inorganic polymer hybrids utilizing the photodimerization of thymine
Imai, Y., Ogoshi, T., Naka, K., et al. (2000) · Polymer Bulletin · doi:10.1007/s002890070050 · Cited by 16 · see citing works
New Tetraalkylborate Initiators for Remote Polymerization
Ermoshkin, A. A., Nikolaeva, E. S., Neckers, D. C., et al. (2008) · Macromolecules · doi:10.1021/ma8007543 · Cited by 14 · see citing works
Role of allylic reversal in free-radical thiol additions to allylic halides
Hall, D. N. (1967) · The Journal of Organic Chemistry · doi:10.1021/jo01282a007 · Cited by 14 · see citing works
Tung, C., Ying, Y., & Yuan, Z. (1998) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/s1010-6030(98)00388-8 · Cited by 3 · see citing works
Kolb (2001) · doi:10.1002/1521-3773(20010601)40:11
Flagged first, then by citations
Research works printed but not linked: 3
- [6]Small JH Loy DA McElhanon JR Saunders RS Method of making thermally removable polymeric encapsalants 7 August 2001 US Patent 6,271,335
- [15]Hoyle CE Lowe AB Chem. Soc. Rev 2009 In Press
- [109]Meistric ML Lamola AA J. Mol. Biol 1972 66 1 83 95 4557199
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Montarnal, D., Capelot, M., Tournilhac, F., & Leibler, L. (2011) · Science · doi:10.1126/science.1212648 · Cited by 3,625 · see citing works
Zhao, Q., Qi, H. J., & Xie, T. (2015) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2015.04.001 · Cited by 1,409 · see citing works
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Meng, H., & Li, G. (2013) · Polymer · doi:10.1016/j.polymer.2013.02.023 · Cited by 1,190 · see citing works
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Kuang, X., Roach, D. J., Wu, J., Hamel, C. M., Ding, Z., Wang, T., Dunn, M. L., & Qi, H. J. (2019) · Advanced Functional Materials · doi:10.1002/adfm.201805290 · Cited by 1,095 · see citing works
Scheutz, G. M., Lessard, J. J., Sims, M. B., & Sumerlin, B. S. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.9b07922 · Cited by 934 · see citing works
Heat‐ or Water‐Driven Malleability in a Highly Recyclable Covalent Network Polymer
Taynton, P., Yu, K., Shoemaker, R. K., Jin, Y., Qi, H. J., & Zhang, W. (2014) · Advanced Materials · doi:10.1002/adma.201400317 · Cited by 890 · see citing works
Dynamic covalent chemistry in polymer networks: a mechanistic perspective
Winne, J. M., Leibler, L., & Du Prez, F. E. (2019) · Polymer Chemistry · doi:10.1039/c9py01260e · Cited by 736 · see citing works
Making Insoluble Polymer Networks Malleable via Olefin Metathesis
Lu, Y.-X., Tournilhac, F., Leibler, L., & Guan, Z. (2012) · Journal of the American Chemical Society · doi:10.1021/ja303356z · Cited by 568 · see citing works
Cleavable comonomers enable degradable, recyclable thermoset plastics
Shieh, P., Zhang, W., Husted, K. E. L., Kristufek, S. L., Xiong, B., Lundberg, D. J., Lem, J., Veysset, D., Sun, Y., Nelson, K. A., et al. (2020) · Nature · doi:10.1038/s41586-020-2495-2 · Cited by 498 · see citing works
Li, L., Chen, X., Jin, K., & Torkelson, J. M. (2018) · Macromolecules · doi:10.1021/acs.macromol.8b00922 · Cited by 424 · see citing works
Delahaye, M., Winne, J. M., & Du Prez, F. E. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.9b07269 · Cited by 334 · see citing works
Various shape memory effects of stimuli-responsive shape memory polymers
Meng, H., Mohamadian, H., Stubblefield, M., Jerro, D., Ibekwe, S., Pang, S.-S., & Li, G. (2013) · Smart Materials and Structures · doi:10.1088/0964-1726/22/9/093001 · Cited by 257 · see citing works
Zheng, N., Hou, J., Xu, Y., Fang, Z., Zou, W., Zhao, Q., & Xie, T. (2017) · ACS Macro Letters · doi:10.1021/acsmacrolett.7b00037 · Cited by 237 · see citing works
Mechanophotopatterning on a Photoresponsive Elastomer
Kloxin, C. J., Scott, T. F., Park, H. Y., & Bowman, C. N. (2011) · Advanced Materials · doi:10.1002/adma.201100323 · Cited by 140 · see citing works
Self-citation
- Authors
- Kloxin, C. J., Scott, T. F., Adzima, B. J., & Bowman, C. N.
- Affiliations
- University of Colorado Boulder (US)
- Corresponding author
- Bowman, Christopher N.
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-02-23
- Volume
- 43
- Issue
- 6
- Pages
- 2643-2653
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- PMC
- PMC2841325
- OpenAlex
- W2094682482
- Cited by
- 1,175
- References
- 110
- Citations by year
- 2026: 136 · 2025: 170 · 2024: 164 · 2023: 157 · 2022: 107 · 2021: 76 · 2020: 84 · 2019: 49 · 2018: 47 · 2017: 33 · 2016: 34 · 2015: 22 · 2014: 19 · 2013: 23 · 2012: 26
- FWCI
- 20.39
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Macromolecules (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institute of Dental and Craniofacial Research (R29DE010959, R01DE010959)
- Topics
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Engineering › Mechanical Engineering › Advanced Materials and Mechanics
- Keywords
- covalent adaptable networks, dynamic covalent bonds, stimuli-responsive polymers, smart materials, thermal stimuli, recyclability, self-healing polymers, shape transformation, tunable materials, polymerization shrinkage stress
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