Reversible Diels-Alder Cycloaddition for the Design of Multifunctional Network Polymers

Click Chemistry for Biotechnology and Materials Science

Volumn , Issue , 2009, Pages 195-215

  Peterson, Amy M ^a   Palmese, Giuseppe R ^a  

^a Drexel University   (United States)

Author keywords

Diels Alder bonds and base polymer material properties; Diels Alder linkages and coupling organic polymer and silica matrix; Diels Alder linkages to polymer systems; Operating and reversing temperatures; Polymer networks and retro Diels Alder reaction on viscoelastic behavior; Polymer networks given additional functionality with incorporation of reversible Diels Alder linkages; Reverse reaction retro Diels Alder reaction; Reversible Diels Alder cycloaddition in multifunctional network polymer design; Reversible Diels Alder linkages and noncrosslinked systems; Thermally remendable polymer based on Diels Alder reaction

Indexed keywords

EID: 84863167370     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470748862.ch9     Document Type: Chapter

References (120)

1. Hartmuth, C., Kolb, M. G. F., (2001), Click chemistry: diverse chemical function from a few good reactions, Angewandte Chemie International Edition, 40 (11), 2004-2021.
2. Sohàr, P., Miklòs, F., Csampai, A., Stàjer, G., (2001), Preparation of pyrimido[2,1-a]phthalazines and an aminopyrimido[2,1-a]isoindole by retro Diels-Alder reaction, Journal of the Chemical Society, Perkin Transactions, 1 (5), 558-564.
3. Stajer, G., Szabo, A., Sohar, P., Csampai, A., Sillanpaa, R., (2006), A retro Diels-Alder method for the preparation of pyrrolo[1,2-a]pyrimidinediones from diexoaminooxanorbornenecarboxamide, Journal of Molecular Structure, 784 (1-3), 239-243.
4. Durmaz, H., Colakoglu, B., Tunca, U., Hizal, G., (2006), Preparation of block copolymers via Diels Alder reaction of maleimide-and anthracene-end functionalized polymers, Journal of Polymer Science Part A: Polymer Chemistry, 44 (5), 1667-1675.
5. Durmaz, H., Karatas, F., Tunca, U., Hizal, G., (2006), Preparation of ABC miktoarm star terpolymer containing poly(ethylene glycol), polystyrene, and poly(tert-butylacrylate) arms by combining Diels-Alder reaction, atom transfer radical, and stable free radical polymerization routes, Journal of Polymer Science Part A: Polymer Chemistry, 44 (1), 499-509.
6. Durmaz, H., Karatas, F., Tunca, U., Hizal, G., (2006), Heteroarm H-shaped terpolymers through the combination of the Diels-Alder reaction and controlled/living radical polymerization techniques, Journal of Polymer Science Part A: Polymer Chemistry, 44 (13), 3947-3957.
7. Nandivada, H., Jiang, X., Lahann, J., (2007), Click chemistry: versatility and control in the hands of materials scientists, Advances in Materials, 19 (17), 2197-2208.
8. Choi, C. K., Tomita, I., Endo, T., (2000), Synthesis of novel pi-conjugated polymer having an enyne unit by palladium-catalyzed three-component coupling polymerization and subsequent retro-Diels-Alder reaction, Macromolecules, 33 (5), 1487-1488.
9. Edelmann, D., Ritter, H., (1993), Synthesis of telechelics with furanyl end-groups by radical polymerisation with azo-initiators and network formation with unsaturated polyesters via Diels-Alder additions, Makromolekular Chemie, 194, 1183.
10. Wassermann, A., (1965), Diels-Alder Reactions. Elsivier Science: Amsterdam.
11. Francesco Finguelli, A. T. (Ed.), (2002), The Diels-Alder Reaction: Selected Practical Methods. John Wiley & Sons Inc.: New York.
12. Nicolaou, K. C., Snyder, S. A.,Montagnon, T.,Vassilikogiannakis, G., (2002), The Diels-Alder reaction in total synthesis, Angewandte Chemie International Edition, 41 (10), 1668-1698.
13. Gandini, A., Belgacem, M. N., (1997), Furans in polymer chemistry, Progress in Polymer Science, 22, 1203.
14. Dewar, M. J. S., Pierini, A. B., (1984), Mechanism of the Diels-Alder reaction. Studies of the addition of maleic anhydride to furan and methylfurans, Journal of the American Chemical Society, 106 (1), 203-208.
15. Laita, H., Boufi, S., Gandini, A., (1997), The application of the Diels-Alder reaction to polymers bearing furan moieties 1. Reactions with maleimides, European Polymer Journal, 33 (8), 1203.
16. Craven, J.M., (1969), Cross-linked thermally reversible polymers produced from condensation polymers with pendant furan groups cross-linked with maleimides. Patent, 3,435,003, 5.
17. McElhanon, J.,Wheeler, D., (2001), Thermally responsive dendrons and dendrimers based on reversible furan-maleimide diels-alder adducts, Organic Letters, 3 (17), 2681-2683.
18. Goussè, C., Gandini,A., Hodge, P., (1998),Application of the Diels-Alder reaction to polymers bearing furan moieties. 2. Diels-Alder and retro-Diels-Alder reactions involving furan rings in some styrene copolymers, Macromolecules, 31 (2), 314-321.
19. Watanabe, M., Yoshie, N., (2006), Synthesis and properties of readily recyclable polymers from bisfuranic terminated poly(ethylene adipate) and multi-maleimide linkers, Polymer, 47 (14), 4946-4952.
20. Liu, Y., Chen, Y., (2007), Thermally reversible cross-linked polyamides with high toughness and self-repairing ability from maleimide-and furan-functionalized aromatic polyamides, Macromolecular Chemistry and Physics, 208 (2), 224-232.
21. Chen, X., Dam, M. A., Ono, K., Mal, A., Shen, H., Nutt, S. R., Sheran, K., Wudl, F., (2002), A Thermally re-mendable cross-linked polymeric material, Science, 295 (5560), 1698-1702.
22. Chen, X., Wudl, F., Mal, A. K., Shen, H., Nutt, S. R., (2003), New thermally remendable highly cross-linked polymeric materials, Macromolecules, 36 (6), 1802-1807.
23. Wudl, F., Chen, X., (2005), Thermally re-mendable cross-linked polymers. Patent, 6,933,361, 21.
24. Mcelhanon, J., Russick, E., Wheeler, D., Loy, D., Aubert, J., (2002), Removable foams based on an epoxy resin incorporating reversible Diels-Alder adducts, Journal of Applied Polymer Science, 85 (7), 1496-1502.
25. Loy, D. A., Wheeler, D. R., Russick, E., Mcelhanon, J. R., Saunders, R. S., (2002), Methods of making thermally removable epoxies. Patent, 6,337,384, 7.
26. Loy, D. A., Wheeler, D. R., Mcelhanon, J. R., Saunders, R. S., (2002), Methods of making thermally removable polyurethanes. Patent, 6,403,753, 13.
27. Kwart, H.,King, K., (1968), The reverseDiels-Alder or retrodiene reaction, Chemistry Review, 68 (4), 415-447.
28. Stevens, M. P., (1979), Crosslinking of polystyrene via pendant maleimide groups, Journal of Polymer Science A Polymer Chemistry, 17 (11), 3675-3685.
29. Tesoro, G. C., Sastri, V. R., (1986), Synthesis of siloxane-containing bis(furans) and polymerization with bis(maleimides), Industrial Engineering Chemistry: Product Research and Development, 25 (3), 444-448.
30. Chujo, Y., Sada, K., Saegusa, T., (1990), Reversible gelation of polyoxazoline by means of Diels-Alder reaction, Macromolecules, 23 (10), 2636-2641.
31. Diakoumakos, C. D., Mikroyannidis, J. A., (1992), Polyimides derived from Diels-Alder polymerization of furfuryl-substituted maleamic acids or from the reaction of bismaleamic with bisfurfurylpyromellitamic acids, Journal of Polymer Science Part A: Polymer Chemistry, 30 (12), 2559-2567.
32. Mikroyannidis, J. A., (1992), Synthesis and Diels-Alder polymerization of furfurylidene and furfuryl-substituted maleamic acids, Journal of Polymer Science Part A: Polymer Chemistry, 30 (1), 125-132.
33. Mikroyannidis, J. A., (1992), Furyl-maleimide in situ generated AB-monomers: synthesis, characterization, and Diels-Alder polymerization, Journal of Polymer Science Part A: Polymer Chemistry, 30 (9), 2017-2024.
34. Kuramoto, N., Hayashi, K., Nagai, K., (1994), Thermoreversible reaction of Diels-Alder polymer composed of difurufuryladipate with bismaleimidodiphenylmethane, Journal of Polymer Science Part A: Polymer Chemistry, 32 (13), 2501-2504.
35. Goussè, C., Gandini, A., (1998), Synthesis of 2-furfurylmaleimide and preliminary study of its Diels-Alder polycondensation, Polymer Bulletin, 40, 389-394.
36. Kamahori, K., Tada, S., Ito, K., Itsuno, S., (1999), Optically active polymer synthesis by diels-alder polymerization with chirally modified Lewis acid catalyst, Macromolecules, 32 (3), 541-547.
37. Imai, Y., Itoh, H., Naka, K., Chujo, Y., (2000), Thermally reversible IPN organic-inorganic polymer hybrids utilizing the Diels-Alder reaction, Macromolecules, 33 (12), 4343-4346.
38. Bibiao, J., Jianjun, H.,Wenyun,W., Luxia, J., Xinxian, C., (2001), Synthesis and properties of novel polybismaleimide oligomers, European Polymer Journal, 37, 463.
39. Small, J. H., Loy, D. A., Wheeler, D. R., Mcelhanon, J. R., Saunders, R. S., (2001), Methods of making thermally removable polymeric encapsulants. Patent, 6,271,335.
40. Gheneim, R., Perez-Berumen, C., Gandini, A., (2002), Diels-Alder Reactions with novel polymeric dienes and dienophiles: synthesis of reversibly cross-linked elastomers, Macromolecules, 35 (19), 7246-7253.
41. Luo, J., Haller, M., Li, H., Kim, T., Jen, A. K., (2003), Highly efficient and thermally stable electro-optic polymer from a smartly controlled crosslinking process, Advances in Materials, 15 (19), 1635-1638.
42. Goiti, E., Huglin, M., Rego, J., (2003), Thermal breakdown by the Retro Diels-Alder reaction of crosslinking in poly[styrene-co-(furfuryl methacrylate)], Macromolecules Rapid Communications, 24 (11), 692-696.
43. Adachi, K., Achimuthu, A. K., Chujo, Y., (2004), Synthesis of organic-inorganic polymer hybrids controlled by Diels-Alder reaction, Macromolecules, 37 (26), 9793-9797.
44. Goiti, E., Heatley, F., Huglin, M., Rego, J. M., (2004), Kinetic aspects of the Diels-Alder reaction between poly(styrene-co-furfuryl methacrylate) and bismaleimide, European Polymer Journal, 40 (7), 1451-1460.
45. Goiti, E., Huglin, M., Rego, J. M., (2004), Some properties of networks produced by the Diels-Alder reaction between poly(styrene-co-furfuryl methacrylate) and bismaleimide, European Polymer Journal, 40 (2), 219-226.
46. Zhang, X., Li, Z. C., Li, K. B., Du, F. S., Li, F. M., (2004),Multi-maleimides bearing electrondonating chromophores: reversible fluorescence and aggregation behavior, Journal of the American Chemical Society, 126 (39), 12200-12201.
47. Costanzo, P. J., Demaree, J. D., Beyer, F. L., (2006), Controlling dispersion and migration of particulate additives with block copolymers and Diels-Alder chemistry, Langmuir, 22, 10251-10257.
48. Costanzo, P. J., Beyer, F. L., (2007), Thermoresponsive, optically active films based on Diels-Alder chemistry, Chemistry Materials, 19 (25), 6168-6173.
49. Gacal, B., Durmaz, H., Tasdelen, M. A., Hizal, G., Tunca, U., Yagci, Y., Demirel, A. L., (2006), Anthracene-maleimide-based Diels-Alder 'click chemistry' as a novel route to graft copolymers, Macromolecules, 39 (16), 5330-5336.
50. Gotsmann, B., Duerig, U., Frommer, J., Hawker, C. J., (2006), Exploiting chemical switching in a Diels-Alder polymer for nanoscale probe lithography and data storage, Advances in Functional Materials, 16 (11), 1499-1505.
51. Liu, Y., Hsieh, C., (2006), Crosslinked epoxy materials exhibiting thermal remendablility and removability from multifunctional maleimide and furan compounds, Journal of Polymer Science A Polymer Chemistry, 44 (2), 905-913.
52. Liu, Y., Hsieh, C., Chen, Y., (2006), Thermally reversible cross-linked polyamides and thermoresponsive gels by means of Diels-Alder reaction, Polymer, 47 (8), 2581-2586.
53. Teramoto, N., Arai, Y., Shibata,M., (2006), Thermo-reversible Diels-Alder polymerization of difurfurylidene trehalose and bismaleimides, Carbohydrate Polymers, 64 (1), 78-84.
54. Brock, P., Chaw, M., Dawson, D., Hawker, C., Hedrick, J., Magbitang, T., McKean, D., Miller, R., Palmisano, R., Volksen,W., (2007), Stable encapsulant fluid capable of undergoing reversible Diels-Alder polymerization. Patent, 7,309,754, 16.
55. Kraiman, E. A., (1959), Maleimide polymers, US Patent, 9 June, 2, 890, 206.
56. Reeder, J. A., (1967), Polyimides from dimaleimides and bisfulvenes. Patent, 3,334,071, 3.
57. Alhakimi, G., Klemm, E., Gorls, H., (1995), Synthesis of new polyimides by Diels-Alder reaction of bis(2-pyrone)s with bismaleimides, Journal of Polymer Science Part A: Polymer Chemistry, 33 (7), 1133-1142.
58. Alhakimi, G., Klemm, E., (1995), Synthesis of a tetra(maleimide) as intermediate compound in a linear Diels-Alder Polyaddition of bismaleimides with bis(2-pyrone)s, Journal of Polymer Science A Polymer Chemistry, 33, 4.
59. Jones, J. R., Liotta, C. L., Collard, D.M., Schiraldi, D. A., (1999), Cross-linking and modification of poly(ethylene terephthalate-co-2,6-anthracenedicarboxylate) by Diels-Alder Reactions with Maleimides, Macromolecules, 32 (18), 5786-5792.
60. Grigoras, M., Colotin, G., (2001), Copolymerization of a bisanthracene compound with bismaleimides by Diels-Alder cycloaddition, Polymer International, 50, 1375-1378.
61. Vargas, M., Kriegel, R. M., Collard, D. M., Schiraldi, D. A., (2002), Diels-Alder modification of poly(ethylene terephthalate-co-anthracene-2,6-carboxylate) with N-substitutedmaleimides, Journal of Polymer Science Part A: Polymer Chemistry, 40 (19), 3256-3263.
62. Kim, C., Kim, H., Park, K., (2003), Diels-Alder reaction of anthracene and N-ethylmaleimide on the carbosilane dendrimer, Journal of Organometallic Chemistry, 667, (1-2), 96-102.
63. Morgenroth, F.,Müllen, K., (1997), Dendritic and hyperbranched polyphenylenes via a simple Diels-Alder route, Tetrahedron, 53 (45), 15349.
64. Morgenroth, F., Kübel, C.,Müller, M.,Wiesler, U.M., Berresheim, A. J.,Wagner, M.,Müllen, K., (1998), From three-dimensional polyphenylene dendrimers to large graphite subunits, Carbon, 36 (5-6), 833.
65. Morgenroth, F., Berresheim, A. J.,Wagner, M.,Müllenö, K., (1998), Spherical polyphenylene dendrimers via Diels-Alder reactions: the first example of an A4B building block in dendrimer chemistry, Chemical Communications, (10), 1139.
66. Yousaf, M. N., Mrksich, M., (1999), Diels-Alder reaction for the selective immobilization of protein to electroactive self-assembled monolayers, Journal of the American Chemical Society, 121 (17), 4286-4287.
67. Yousaf, M. N., Chan, E. W. L., Mrksich, M., (2000), The kinetic order of an interfacial diels-alder reaction depends on the environment of the immobilized dienophile, Angewandte Chemie International Edition, 39 (11), 1943-1946.
68. Kwon, Y., Mrksich, M., (2002), Dependence of the rate of an interfacial Diels-Alder reaction on the steric environment of the immobilized dienophile: an example of enthalpy-entropy compensation, Journal of American Chemical Society, 124 (5), 806-812.
69. Gawalt, E. S., Mrksich, M., (2004), A Substituent Effects Study Reveals the Kinetic Pathway for an Interfacial Reaction, Journal of American Chemical Society, 126 (47), 15613-15617.
70. Upson, R. W., (1955), P-Xylene Bis(5-cyclopentadiene) and Polymer. Patent, 2,726,232, 4.
71. Herndon, W. C., Grayson, C. R., Manion, J. M., (1967), Retro-Diels-Alder reactions. III. Kinetics of the thermal decompositions of exo-and endo-dicyclopentadiene, Journal of Organic Chemistry, 32 (3), 526-529.
72. Kennedy, J. P., Castner, K. F., (1979), Thermally reversible polymer systems by cyclopentadienylation. II. The synthesis of cyclopentadiene-containing polymers, Journal of Polymer Science: Polymer Chemistry Edition, 17 (7), 2055-2070.
73. Kennedy, J. P., Castner, K. F., (1979), Thermally reversible polymer systems by cyclopentadienylation. I. A model for termination by cyclopentadienylation of olefin polymerization, Journal of Polymer Science: Polymer Chemistry Edition, 17 (7), 2039-2054.
74. Kennedy, J., Carlson, G., (1983), Synthesis, characterization, and Diels-Alder extension of cyclopentadiene telechelic polyisobutylene. IV. alpha,omega-Di(3-cyclopentadienylpropyldimethylsilyl) polyisobutylene, Journal of Polymer Science: Polymer Chemistry Edition, 21 (12), 3551-3561.
75. Murphy, E. B., Bolanos, E., Schaffner-Hamann, C.,Wudl, F., Nutt, S. R., Auad, M. L., (2008), Synthesis and characterization of a single-component thermally remendable polymer network: Staudinger and Stille revisited, Macromolecules, 41 (9), 3169-3174.
76. Stille, J. K., Plummer, L., (1961), Polymerization by the Diels-Alder reaction, Journal of Organic Chemistry, 26 (10), 4026-4029.
77. Takeshita, Y., Uoi, M., Hirai, Y., Uchiyama, M., (1974), Thermoplastic plastic composition. Patent, 3,826,760, 9.
78. Miura, M., Akutsu, F., Ursui, T., Ikebukuro, Y., Nagakubo, K., (1985), Soluble cyclopentadienylated polymers, Makromolekulare Chemie, 186, 473-481.
79. Salamone, J. C., Chung, Y., Clough, S. B., Watterson, A. C., (1988), Thermally reversible, covalently crosslinked polyphosphazenes, Journal of Polymer Science Part A: Polymer Chemistry, 26 (11), 2923-2939.
80. Canary, S. A., Stevens, M., (1992), Thermally reversible crosslinking of polystyrene via the furan-maleimide Diels-Alder reaction, Journal of Polymer Science A Polymer Chemistry, 30 (8), 1755-1760.
81. Kelen, T., Ivàn, B., Nagy, T. T., Turcsànyi, B., Tüdös, F., Kennedy, J. P., (1978), Reversible crosslinking during thermal degradation of PVC, Polymer Bulletin, 1 (2), 79-84.
82. Ivàn, B., Nagy, T. T., Kelen, T., Turcsànyi, B., Tüdös, F., (1980), Crosslinking and scission in thermooxidative degradation of PVC, Polymer Bulletin, 2 (1), 83-88.
83. Nagy, T. T., Ivàn, B., Turcsànyi, B., Kelen, T., Tüdös, F., (1980), Crosslinking, scission and benzene formation during PVC degradation under various conditions, Polymer Bulletin, 3 (11), 613-620.
84. Neukam, W., Grimme, W., (1978), Anionic [4+2]-cycloreversions leading to the cyanocyclopentadienide ion, Tetrahedron Letters, 19 (25), 2201.
85. Kwart, H., Burchuk, I., (1952), Isomerism and adduct stability in the Diels-Alder Reaction. I. The adducts of furan and maleimide, Journal of the American Chemical Society, 74, 3094-3097.
86. Papies, O., Grimme, W., (1980), Acceleration of the [4 + 2]-cycloreversion by the alkoxide substituent, Tetrahedron Letters, 21, 2799.
87. Brand, T., Klapper, M., (1999), Control of viscosity through reversible addition of telechelics via repetitive Diels-Alder reaction in bulk, Designed Monomers and Polymers, 2 (4), 287-309.
88. Edelmann, D., Ritter, H., (1993), Synthesis of telechelics with furanyl end-groups, 2: Radical polymerisation with C-C-bond splitting initiators and network formation with unsaturated polyesters via Diels-Alder additions, Makromolekulare Chemie, 194, 2375-2384.
89. Ritter, H., Sperber, R., Weisshuhn, C. M., (1993), Reactive comb-like polymers. Kinetic studies of the Diels-Alder reaction of furan-containing comb-like polymers with dimethyl butyndioate by means of 1H NMR spectroscopy, Makromolekulare Chemie, 194, 1721-1731.
90. Cowie, J. M. G., (1991), Polymers: Chemistry & Physics of Modern Materials. CRC Press: Boca Raton, FL, p. 431.
91. Zhu, J., Kell, A. J., Workentin, M. S., (2006), A retro-Diels-Alder reaction to uncover maleimide-modified surfaces on monolayer-protected nanoparticles for reversible covalent assembly, Organic Letters, 8 (22), 4993-4996.
92. Hao, J., Wang, W., Jiang, B., Cai, X., Jiang, L., (1999), Preparation, solubility and thermal behaviour of new bismaleimides containing silicone linkages, Polymer International, 48, 235-243.
93. Jenkins, A. D., Kratochvil, P., Stepto, R. F. T., Suter, U.W., (1996), Glossary of basic terms in polymer science, Pure and Applied Chemistry, 68 (12), 2287-2311.
94. Engle, L. P., Wagener, K. B., (1993), A review of thermally controlled covalent bond formation in polymer chemistry, Journal of Macromolecular Science: Reviews in Macromolecular Chemistry and Physics, 33 (3), 239-257.
95. Bergman, S., Wudl, F., (2008), Mendable polymers, Journal of Materials Chemistry, 18 (1), 41.
96. Wool, R. P., (2008), Self-healing materials: a review, Soft Matter; DOI: 10.1039/ B711716G.
97. Leibler, L., Rubinstein, M., Colby, R. H., (1991), Dynamics of reversible networks, Macromolecules, 24 (16), 4701-4707.
98. Flory, P. J., (1941), Molecular size distribution in three dimensional polymers, I. Gelation. Journal of American Chemical Society, 63 (11), 3083-3090.
99. Flory, P. J., (1941),Molecular size distribution in three dimensional polymers. II. Trifunctional branching units, Journal of American Chemical Society, 63 (11), 3091-3096.
100. Stockmayer, W. H., (1943), Theory of molecular size distribution and gel formation in branched-chain polymers, Journal of Chemistry Phys., 11 (2), 45-55.
101. Stockmayer,W. H., (1944), Theory of molecular size distribution and gel formation in branched polymers II. General cross linking, Journal of Chemistry Phys., 12 (4), 125-131.
102. Williams, M. L., Landel, R. F., Ferry, J. D., The temperature dependence of relaxation mechanisms in amorphous polymers and other glass-forming liquids. Journal of the American Chemical Society 1955, 77, 3701-3707.
103. Chow, S., John M. Whelan, J., (1961), Maleimide polymers. Patent, 2,971,944, 5.
104. Harris, F. W., Stille, J. K., (1968), Diels-Alder polymers. Polyimides from a biscyclopentadienone and bismaleimides, Macromolecules, 1 (5), 463-464.
105. Wagener, K. B., Engle, L. P., (1993), Thermally reversible polymer linkages. II. Linear addition polymers, Journal of Polymer Science A Polymer Chemistry, 31 (4), 865-875.
106. Kintzel, O., Luger, P., Weber, M., Schlüter, A., (1998), Ring-chain equilibrium between an [18]cyclacene derivative and a ladder oligomer, European Journal of Organic Chemistry, (1), 99.
107. Diakoumakos, C. D., Mikroyannidis, J. A., (1994), Heat-resistant resins derived from cyanosubstituted Diels-Alder polymers, European Polymer Journal, 30 (4), 465-472.
108. Blatter, K., Schlueter, A., (1989), Model studies for the synthesis of ribbon-shaped structure by repetitive Diels-Alder reaction, Chemische Berichte, 122, 1351-1356.
109. Blatter, K., Schlueter, A. D., (1989), Ribbon-shaped structures via repetitive Diels-Alder reaction. A polycatafusene, Macromolecules, 22 (8), 3506-3508.
110. Sedghat-Herati, M. R., (2000), Synthesis and characterization of 5-[methoxypoly(oxyethylene)]-(3E)-1,3-pentadiene and its Diels-Alder reactions, Macromolecules, 33 (6), 1924-1925.
111. Hopkins, T. E., Park, M., Chacon, A., Sedaghat-Herati, R., (2005), New poly(oxyethylene) derivatives and their oligo analogues from Diels-Alder reactions of 5-[methoxypoly(oxyethylene)]-(3E)-1,3-pentadiene and 5-methoxyethoxy-(3E)-1,3-pentadiene, Journal of Polymer Science Part A: Polymer Chemistry, 43 (9), 1895-1902.
112. Goiti, E., Huglin, M., Rego, J. M., (2001), Some observations on the copolymerization of styrene with furfuryl methacrylate, Polymer, 42, 10187-10193.
113. Peterson, A. M., Jensen, R. E., Palmese, G. R., (2009), Reversibly cross-linked polymer gels as healing agents for epoxy-amine thermosets, ACS Applied Materials & Interfaces, 1(5), 00-00.
114. Plaisted, T. A., Nemat-Nasser, S., (2007), Quantitative evaluation of fracture, healing and re-healing of a reversibly cross-linked polymer, Acta Materialia, 55 (17), 5684-5696.
115. White, S. R., Sottos, N. R., Geubelle, P. H., Moore, J. S., Kessler,M., Sriram, S. R., Brown, E. N., Viswanathan, S., (2001), Autonomic healing of polymer composites, Nature, 409 (6822), 794-797.
116. Plaisted, T. A., Amirkhizi, A. V., Arbelaez, D., Nemat-Nasser, S. C., Nemat-Nasser, S., (2003), Self-healing Structural Composites with Electromagnetic Functionality, Proceedings of SPIE, pp. 372-381.
117. Kavitha, A. A., Singha, N. K., (2007), A tailor-made polymethacrylate bearing a reactive diene in reversible Diels-Alder reaction, Journal of Polymer Science A Polymer Chemistry, 45 (19), 4441-4449.
118. Nakano, M., Usuki, A., Okada, A., Kamigaito, O., (1997), Recyclabe polymer, process for producing the same, method for recovering the same, and method for regenerating the same. Patent, 5,643,998, 16.
119. Reinecke, M., Ritter, H., (1993), Renewable resources, 1: branching and crosslinking of an unsaturated oligoester with furfurylamides and sorbic acid amides via Diels-Alder additions, Makromolekulare Chemie, 194, 2385-2393.
120. Kim, T., Luo, J., Tian, Y., Ka, J., Tucker, N. M., Haller, M., Kang, J., Jen, A. K., (2006), Diels-Alder 'click chemistry' for highly efficient electrooptic polymers, Macromolecules, 39 (5), 1676-1680.