Alternating Copolymers Based on Amino Acids and Peptides

  • Ishita Mukherjee
  • Krishna Gopal Goswami
  • Priyadarsi DeEmail author
Part of the Materials Horizons: From Nature to Nanomaterials book series (MHFNN)


Controlling the monomer sequence along the polymer chain leads to the development of a special class of synthetic copolymers, and they are known as alternating copolymers when the two comonomers are placed in a regular exchanging fashion. The monomer sequence control plays an important role to regulate the different bulk properties such as conductivity, rigidity, biodegradability, as well as mimic the properties of the sequence defined biopolymers like DNA, RNA, enzymes, and proteins. Very recently, different synthetic strategies have been explored to mimic the monomer sequences in synthetic polymeric materials. An enormous combination of several desired functionalities has been attached with the electron donor styrene, stilbene or electron acceptor maleic anhydride or N-substituted maleimide moieties to produce strictly alternating backbone and their properties have been extensively investigated. Nowadays, functionalities like amino acids and peptides, essential and fundamental components of protein biopolymers and alive entities extending from bacteria to humans with a variety of enormities from nano to macro dimension, are widely used to design an extensive range of block or random copolymers with significant assets and applications, as they can play critical responsibility in both functional and structural levels. The multifaceted biological features of these moieties help to generate bioactive and biocompatible materials. However, the properties associated with their alternating architecture have not been broadly studied. By providing a quick look on different types of alternating copolymers, in this book chapter, we aim to focus on recent developments of amino acid and peptide-based alternating architectures, their interesting properties and applications as bioinspired nanomaterials, in inclusion chemistry, catalysis, sensing, tissue engineering, molecular electronics, molecular separation technology, and so on.


Alternating copolymers Amino acids and peptides Biopolymers Building block 



I. M. and K. G. G. acknowledge Council of Scientific and Industrial Research (CSIR), Government of India, India, for their research fellowships.


  1. 1.
    Matyjaszewski K (2005) Macromolecular engineering: from rational design through precise macromolecular synthesis and processing to targeted macroscopic material properties. Prog Polym Sci 30:858–875. Scholar
  2. 2.
    (a) Pyun J, Zhou XZ, Drockenmuller E, Hawker CJ (2003) Macromolecules of controlled architecture. J Mat Chem 13:2653–2660.; (b) Bernaerts KV, Du Prez FE (2006) Dual/heterofunctional initiators for the combination of mechanistically distinct polymerization techniques. Prog Polym Sci 31:671–722.; (c) Lutz J-F (2007) 1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science. Angew Chem Int Ed 46:1018–1025.; (d) McCormick CL, Sumerlin BS, Lokitz BS, Stempka JE (2008) RAFT-synthesized diblock and triblock copolymers: thermally-induced supramolecular assembly in aqueous media. Soft Matter 4:1760–1773.; (e) Moad G, Rizzardo E, Thang SH (2008) Radical addition–fragmentation chemistry in polymer synthesis. Polymer 49:1079–1131.
  3. 3.
    Yokota K (1999) Periodic copolymers. Prog Polym Sci 24:517–563. Scholar
  4. 4.
    Matyjaszewski K, Ziegler MJ, Arehart SV, Greszta D, Pakula T (2000) Gradient copolymers by atom transfer radical copolymerization. J Phys Org Chem 13:775–786.;2-DCrossRefGoogle Scholar
  5. 5.
    Lutz J-F (2014) Aperiodic copolymers. ACS Macro Lett 3:1020–1023. Scholar
  6. 6.
    Badi N, Chan-Seng D, Lutz J-F (2013) Microstructure control: an underestimated parameter in recent polymer design. Macromol Chem Phys 214:135–142. Scholar
  7. 7.
    Lutz J-F (2010) A controlled sequence of events. Nat Chem 2:84–85. Scholar
  8. 8.
    Badi N, Lutz J-F (2009) Sequence control in polymer synthesis. Chem Soc Rev 38:3383–3390. Scholar
  9. 9.
    Ouchi M, Badi N, Lutz J-F, Sawamoto M (2011) Single-chain technology using discrete synthetic macromolecules. Nat Chem 3:917–924. Scholar
  10. 10.
    Lutz J-F (2010) Sequence-controlled polymerizations: the next Holy Grail in polymer science? Polym Chem 1:55–62. Scholar
  11. 11.
    Schmidt BVKJ, Fechler N, Falkenhagen J, Lutz J-F (2011) Controlled folding of synthetic polymer chains through the formation of positionable covalent bridges. Nat Chem 3:234–238. Scholar
  12. 12.
    Lutz J-F, Ouchi M, Liu DR, Sawamoto M (2013) Sequence-controlled polymers. Science 341:628–636.
  13. 13.
    Espeel P, Carrette LLG, Bury K, Capenberghs S, Martins JC, Du Prez FE, Madder A (2013) Multifunctionalized sequence-defined oligomers from a single building block. Angew Chem Int Ed 52:13261–13264. Scholar
  14. 14.
    Solleder SC, Meier MAR (2014) Sequence control in polymer chemistry through the Passerini three-component reaction. Angew Chem Int Ed 53:711–714. Scholar
  15. 15.
    Satoh K, Ozawa S, Mizutani M, Nagai K, Kamigaito M (2010) Sequence-regulated vinyl copolymers by metal-catalysed step-growth radical polymerization. Nat Commun 1:1–6. Scholar
  16. 16.
    Niu J, Hili R, Liu DR (2013) Enzyme-free translation of DNA into sequence-defined synthetic polymers structurally unrelated to nucleic acids. Nat Chem 5:282–292. Scholar
  17. 17.
    Zhang Q, Collins J, Anastasaki A, Wallis R, Mitchell DA, Becer CR, Haddleton DM (2013) Sequence-controlled multi-block glycopolymers to inhibit DC-SIGN-gp120 binding. Angew Chem 125:4531–4535. Scholar
  18. 18.
    Gody G, Maschmeyer T, Zetterlund PB, Perrier S (2013) Rapid and quantitative one-pot synthesis of sequence-controlled polymers by radical polymerization. Nat Commun 4:2505 (1–9).
  19. 19.
    Pfeifer S, Lutz J-F (2007) A facile procedure for controlling monomer sequence distribution in radical chain polymerizations. J Am Chem Soc 129:9542–9543.
  20. 20.
    Satoh K, Matsuda M, Nagai K, Kamigaito M (2010) A AB-sequence living radical chain copolymerization of naturally occurring limonene with maleimide: an end-to-end sequence-regulated copolymer. J Am Chem Soc 132:10003–10005. Scholar
  21. 21.
    IUPAC (1997) Compendium of chemical terminology (the “Gold Book”), 2nd edn. Blackwell Scientific Publications, OxfordGoogle Scholar
  22. 22.
    Odian G (2004) Principles of polymerization. Wiley, Hoboken, NJCrossRefGoogle Scholar
  23. 23.
    Huang J, Turner SR (2017) Recent advances in alternating copolymers: the synthesis, modification, and applications of precision polymers. Polymer 116:572–586. Scholar
  24. 24.
    Berthet M-A, Zarafshani Z, Pfeifer S, Lutz J-F (2010) Facile synthesis of functional periodic copolymers: a step toward polymer-based molecular arrays. Macromolecules 43:44–50. Scholar
  25. 25.
    Ramakers BEI, van Hest JCM, Lowik DWPM (2014) Molecular tools for the construction of peptide-based materials. Chem Soc Rev 43:2743–2756. Scholar
  26. 26.
    Deng C, Wu J, Cheng R, Meng F, Klok H-A, Zhong Z (2014) Functional polypeptide and hybrid materials: precision synthesis via α-amino acid N-carboxyanhydride polymerization and emerging biomedical applications. Prog Polym Sci 39:330–364. Scholar
  27. 27.
    Secker C, Brosnan SM, Luxenhofer R, Schlaad H (2015) Poly(α-peptoid)s revisited: synthesis, properties, and use as biomaterial. Macromol Biosci 15:881–891. Scholar
  28. 28.
    Sedman VL, Chen X, Allen S, Roberts CJ, Korolkov VV, Tendler SJB (2013) Tuning the mechanical properties of self-assembled mixed-peptide tubes. J Microsc 249:165–172. Scholar
  29. 29.
    Orbach R, Mironi-Harpaz I, Adler-Abramovich L, Mossou E, Mitchell EP, Forsyth VT, Gazit E, Seliktar D (2012) The rheological and structural properties of fmoc-peptide-based hydrogels: the effect of aromatic molecular architecture on self-assembly and physical characteristics. Langmuir 28:2015–2022. Scholar
  30. 30.
    Bauri K, Pant S, Roy SG, De P (2013) Dual pH and temperature responsive helical copolymer libraries with pendant chiral leucine moieties. Polym Chem 4:4052–4060. Scholar
  31. 31.
    Kumar S, Acharya R, Chatterji U, De P (2013) Side-chain amino-acid-based ph-responsive self-assembled block copolymers for drug delivery and gene transfer. Langmuir 29:15375–15385. Scholar
  32. 32.
    Alfrey T, Lavin E (1945) The copolymerization of styrene and maleic anhydride. J Am Chem Soc 67:2044–2045. Scholar
  33. 33.
    Oishi A, Matsuoka H, Yasuda T, Watanabe M (2009) Novel styrene/N-phenylmaleimide alternating copolymers with pendant sulfonimide acid groups for polymer electrolyte fuel cell applications. J Mater Chem 19:514–521. Scholar
  34. 34.
    Mohamed MG, Hsu K-C, Hong J-L, Kuo S-W (2016) Unexpected fluorescence from maleimide-containing polyhedral oligomeric silsesquioxanes: nanoparticle and sequence distribution analyses of polystyrene-based alternating copolymers. Polym Chem 7:135–145. Scholar
  35. 35.
    Qiu G-M, Zhu B-K, Xu Y-Y, Geckeler KE (2006) Synthesis of ultrahigh molecular weight poly(styrene-alt-maleic anhydride) in supercritical carbon dioxide. Macromolecules 39:3231–3237. Scholar
  36. 36.
    Wu D-C, Hong C-Y, Pan C-Y, He W-D (2003) Study on controlled radical alternating copolymerization of styrene with maleic anhydride under UV irradiation. Polym Int 52:98–103. Scholar
  37. 37.
    Montaudo MS (2001) Determination of the compositional distribution and compositional drift in styrene/maleic anhydride copolymers. Macromolecules 34:2792–2797. Scholar
  38. 38.
    Klumperman B (2010) Mechanistic considerations on styrene–maleic anhydride copolymerization reactions. Polym Chem 1:558–562. Scholar
  39. 39.
    Benoit D, Hawker CJ, Huang EE, Lin Z, Russell TP (2000) One-step formation of functionalized block copolymers. Macromolecules 33:1505–1507. Scholar
  40. 40.
    Wang Y, Shen Y, Pei X, Zhang S, Liu H, Ren J (2008) In situ synthesis of poly(styrene-co-maleic anhydride)/SiO2 hybrid composites via “grafting onto” strategy based on nitroxide-mediated radical polymerization. React Funct Polym 68:1225–1230. Scholar
  41. 41.
    Williams EGL, Fairbanks B, Moad G, Mulder RJ, Rizzardo E, Thang SH (2015) Preparation of 1:1 alternating, nucleobase-containing copolymers for use in sequence-controlled polymerization. Polym Chem 6:228–232. Scholar
  42. 42.
    Wang S, Wu B, Liu F, Gao Y, Zhang W (2015) A well-defined alternating copolymer based on a salicylaldimine Schiff base for highly sensitive zinc(II) detection and pH sensing in aqueous solution. Polym Chem 6:1127–1136. Scholar
  43. 43.
    Saha B, Bauri K, Bag A, Ghorai PK, De P (2016) Conventional fluorophore-free dual pH- and thermo-responsive luminescent alternating copolymer. Polym Chem 7:6895–6900. Scholar
  44. 44.
    Wenyan H, Huili P, Bibiao J, Qiang R, Guangqun Z, Lizhi K, Dongliang Z, Jianhai C (2011) Preparation of heat-resistant branched poly(styrene-alt-NPMI) by ATRP with divinylbenzene as the branching agent. J Appl Polym Sci 119:977–982. Scholar
  45. 45.
    Chen GQ, Wu ZQ, Wu JR, Li ZC, Li FM (2000) Synthesis of alternating copolymers of n-substituted maleimides with styrene via atom transfer radical polymerization. Macromolecules 33:232–234. Scholar
  46. 46.
    Lutz J-F, Schmidt BVKJ, Pfeifer S (2011) Tailored polymer microstructures prepared by atom transfer radical copolymerization of styrene and n-substituted maleimides. Macromol Rapid Commun 32:127–135. Scholar
  47. 47.
    Sanders GC, Duchateau R, Lin CY, Coote ML, Heuts JPA (2012) End-functional styrene–maleic anhydride copolymers via catalytic chain transfer polymerization. Macromolecules 45:5923–5933. Scholar
  48. 48.
    Longo JM, DiCiccio AM, Coates GW (2014) Poly(propylene succinate): a new polymer stereocomplex. J Am Chem Soc 136:15897–15900. Scholar
  49. 49.
    Kramer JW, Treitler DS, Dunn EW, Castro PM, Roisnel T, Thomas CM, Coates GW (2009) Polymerization of enantiopure monomers using syndiospecific catalysts: a new approach to sequence control in polymer synthesis. J Am Chem Soc 131:16042–16044. Scholar
  50. 50.
    Li J, He J (2015) Synthesis of sequence-regulated polymers: alternating polyacetylene through regioselective anionic polymerization of butadiene derivatives. ACS Macro Lett 4:372–376. Scholar
  51. 51.
    Stayshich RM, Meyer TY (2008) Preparation and microstructural analysis of poly(lactic-alt-glycolic acid). J Polym Sci Part A Polym Chem 46:4704–4711. Scholar
  52. 52.
    Tsuji H, Arakawa Y (2018) Synthesis, properties, and crystallization of the alternating stereocopolymer poly(L-lactic acid-alt-D-lactic acid) [syndiotactic poly(lactic acid)] and its blend with isotactic poly(lactic acid). Polym Chem 9:2446–2457. Scholar
  53. 53.
    Mayo FR, Lewis FM (1944) Copolymerization. I. A basis for comparing the behavior of monomers in copolymerization; the copolymerization of styrene and methyl methacrylate. J Am Chem Soc 66:1594–1601. Scholar
  54. 54.
    Fukuda T, Ma Y-D, Kubo K, Inagaki H (1991) Penultimate-unit effects in free-radical copolymerization. Macromolecules 24:370–375. Scholar
  55. 55.
    Sanayei RA, O’Driscoll KF, Klumperman B (1994) Pulsed laser copolymerization of styrene and maleic anhydride. Macromolecules 27:5577–5582. Scholar
  56. 56.
    Fukuda T, Kubo K, Ma Y-D (1992) Kinetics of free radical copolymerization. Prog Polym Sci 17:875–916. Scholar
  57. 57.
    Jones SA, Prementine GS, Tirrell DA (1985) Model copolymerization reactions. Direct observation of a “penultimate effect” in a model styrene-acrylonitrile copolymerization. J Am Chem Soc 107:5275–5276. Scholar
  58. 58.
    Tsuchida E, Tomono T (1971) Discussion on the mechanism of alternating copolymerization of styrene and maleic anhydride. Makromol Chem 141:265–298. Scholar
  59. 59.
    Zhao Y, Li H, Liu P, Liu H, Jiang J, Xi F (2002) Reactivity ratios of free monomers and their charge-transfer complex in the copolymerization of N-butyl maleimide and styrene. J Appl Polym Sci 83:3007–3012. Scholar
  60. 60.
    Dodgson K, Ebdon JR (1977) On the role of monomer—monomer donor—acceptor complexes in the free-radical copolymerisation of styrene and maleic anhydride. Eur Polym J 13:791–797. Scholar
  61. 61.
    Deb PC, Meyerhoff G (1985) Study on kinetics of copolymerization of styrene and maleic anhydride in methyl ethyl ketone. Polymer 26:629–635. Scholar
  62. 62.
    Hall HK, Padias AB (2001) “Charge transfer” polymerization—and the absence thereof! J Polym Sci Part A Polym Chem 39:2069–2077. Scholar
  63. 63.
    Haldar U, Pan A, Mukherjee I, De P (2016) POSS semitelechelic Aβ17–19 peptide initiated helical polypeptides and their structural diversity in aqueous medium. Polym Chem 7:6231–6240. Scholar
  64. 64.
    Heitz F, Spach G (1971) Synthesis and conformational study of alternating poly(γ-benzyl D,L-glutamates). Macromolecules 4:429–432. Scholar
  65. 65.
    Seipke G, Arfmann H-A, Wagner KG (1974) Synthesis and properties of alternating poly(Lys-Phe) and comparison with the random copolymer poly(Lys51, Phe49). Biopolymers 13:1621–1633. Scholar
  66. 66.
    Li G, Raman VK, Xie W, Gross RA (2008) Protease-catalyzed co-oligomerizations of L-leucine ethyl ester with L-glutamic acid diethyl ester: sequence and chain length distributions. Macromolecules 41:7003–7012. Scholar
  67. 67.
    DiMarco RL, Heilshorn SC (2012) Multifunctional materials through modular protein engineering. Adv Mater 24:3923–3940. Scholar
  68. 68.
    Garanger E, Lecommandoux S (2012) Towards bioactive nanovehicles based on protein polymers. Angew Chem Int Ed 51:3060–3062. Scholar
  69. 69.
    Ghadiri MR, Granja JR, Milligan RA, McRee DE, Khazanovich N (1993) Self-assembling organic nanotubes based on a cyclic peptide architecture. Nature 366:324–327. Scholar
  70. 70.
    Al Samad A, De Winter J, Gerbaux P, Jerome C, Debuigne A (2017) Unique alternating peptide–peptoid copolymers from dipeptides via a Ugi reaction in water. Chem Commun 53:12240–12243. Scholar
  71. 71.
    Schneider JP, Pochan DJ, Ozbas B, Rajagopal K, Pakstis L, Kretsinger J (2002) Responsive hydrogels from the intramolecular folding and self-assembly of a designed peptide. J Am Chem Soc 124:15030–15037. Scholar
  72. 72.
    Pochan DJ, Schneider JP, Kretsinger J, Ozbas B, Rajagopal K, Haines L (2003) Thermally reversible hydrogels via intramolecular folding and consequent self-assembly of a de novo designed peptide. J Am Chem Soc 125:11802–11803. Scholar
  73. 73.
    Ozbas B, Kretsinger J, Rajagopal K, Schneider JP, Pochan DJ (2004) Salt-triggered peptide folding and consequent self-assembly into hydrogels with tunable modulus. Macromolecules 37:7331–7337. Scholar
  74. 74.
    Kretsinger JK, Haines LA, Ozbas B, Pochan DJ, Schneider JP (2005) Cytocompatibility of self-assembled β-hairpin peptide hydrogel surfaces. Biomaterials 26:5177–5186. Scholar
  75. 75.
    Frisch H, Besenius P (2015) pH-Switchable self-assembled materials. Macromol Rapid Commun 36:346–363. Scholar
  76. 76.
    Frisch H, Nie Y, Raunser S, Besenius P (2015) pH-Regulated selectivity in supramolecular polymerizations: switching between co- and homopolymers. Chem Eur J 21:3304–3309. Scholar
  77. 77.
    Ebert G, Kuroyanagi Y (1982) Salt effect on the conformation of an alternating copolymer of L-leucine and L-lysine. Polymer 23:1154–1158. Scholar
  78. 78.
    Higuchi M, Nagata K, Abiko S, Tanaka M, Kinoshita T (2008) Stimuli induced structural changes of gold nanoparticle assemblies having sequential alternating amphiphilic peptides at the surface. Langmuir 24:13359–13363. Scholar
  79. 79.
    Grieshaber SE, Farran AJE, Lin-Gibson S, Kiick KL, Jia X (2009) Synthesis and characterization of elastin–mimetic hybrid polymers with multiblock, alternating molecular architecture and elastomeric properties. Macromolecules 42:2532–2541. Scholar
  80. 80.
    Grieshaber SE, Nie T, Yan C, Zhong S, Teller SS, Clifton RJ, Pochan DJ, Kiick KL, Jia X (2011) Assembly properties of an alanine-rich, lysine-containing peptide and the formation of peptide/polymer hybrid hydrogels. Macromol Chem Phys 212:229–239. Scholar
  81. 81.
    Kricheldorf HR, Hauser K (2001) Polylactones, 45. Homo- and copolymerizations of 3-methylmorpholine-2,5-dione initiated with a cyclic tin alkoxide. Macromol Chem Phys 202:1219–1226.;2-UCrossRefGoogle Scholar
  82. 82.
    Feng Y, Guo J (2009) Biodegradable polydepsipeptides. Int J Mol Sci 10:589–615. Scholar
  83. 83.
    Franz N, Klok H-A (2010) Synthesis of functional polydepsipeptides via direct ring-opening polymerization and post-polymerization modification. Macromol Chem Phys 211:809–820. Scholar
  84. 84.
    Ouchi T, Hamada A, Ohya Y (1999) Biodegradable microspheres having reactive groups prepared from L-lactic acid-depsipeptide copolymers. Macromol Chem Phys 200:436–441.;2-6CrossRefGoogle Scholar
  85. 85.
    Ouchi T, Toyohara M, Arimura H, Ohya Y (2002) Preparation of poly(L-lactide)-based microspheres having a cationic or anionic surface using biodegradable surfactants. Biomacromolecules 3:885–888. Scholar
  86. 86.
    He Y, Du YR, Liu XB (2011) Synthesis, characterization and properties of polyesteramides based on ε-caprolactone and 6-aminocaproic acid. Adv Mat Res 287–290:1538–1547. Scholar
  87. 87.
    Qian Z, He Y, Zou Y, Li S, Liu X (2004) Structure and property study of degradable polyesteramide fibres: processing and alkaline degradation behaviour. Polym Degrad Stab 83:127–132. Scholar
  88. 88.
    Ali Mohamed A, Salhi S, Abid S, El Gharbi R, Fradet A (2014) Random and quasi-alternating polyesteramides deriving from ε-caprolactone and β-alanine. Eur Polym J 53:160–170. Scholar
  89. 89.
    Tsuji H (2016) Poly(lactic acid) stereocomplexes: a decade of progress. Adv Drug Deliv Rev 107:97–135. Scholar
  90. 90.
    Tsuji H, Sato S, Masaki N, Arakawa Y, Kuzuya A, Ohya Y (2018) Synthesis, stereocomplex crystallization and homo-crystallization of enantiomeric poly(lactic acid-co-alanine)s with ester and amide linkages. Polym Chem 9:565–575. Scholar
  91. 91.
    Matsui H, Ueda M, Makino A, Kimura S (2012) Molecular assembly composed of a dendrimer template and block polypeptides through stereocomplex formation. Chem Commun 48:6181–6183. Scholar
  92. 92.
    Ueda M, Makino A, Imai T, Sugiyama J, Kimura S (2011) Transformation of peptide nanotubes into a vesicle via fusion driven by stereo-complex formation. Chem Commun 47:3204–3206. Scholar
  93. 93.
    Ueda M, Makino A, Imai T, Sugiyama J, Kimura S (2011) Tubulation on peptide vesicles by phase-separation of a binary mixture of amphiphilic right-handed and left-handed helical peptides. Soft Matter 7:4143–4146. Scholar
  94. 94.
    Grieshaber SE, Paik BA, Bai S, Kiick KL, Jia X (2013) Nanoparticle formation from hybrid, multiblock copolymers of poly(acrylic acid) and a VPGVG peptide. Soft Matter 9:1589–1599. Scholar
  95. 95.
    Graña-Suárez L, Verboom W, Buckle T, Rood M, van Leeuwen FWB, Huskens J (2016) Loading and release of fluorescent oligoarginine peptides into/from pH-responsive anionic supramolecular nanoparticles. J Mater Chem B 4:4025–4032. Scholar
  96. 96.
    Zhou C, Yuan Y, Zhou P, Wang F, Hong Y, Wang N, Xu S, Du J (2017) Highly effective antibacterial vesicles based on peptide-mimetic alternating copolymers for bone repair. Biomacromolecules 18:4154–4162. Scholar
  97. 97.
    Bauri K, Saha B, Mahanti J, De P (2017) A nonconjugated macromolecular luminogen for speedy, selective and sensitive detection of picric acid in water. Polym Chem 8:7180–7187. Scholar
  98. 98.
    Srichan S, Chan-Seng D, Lutz J-F (2012) Influence of strong electron-donor monomers in sequence-controlled polymerizations. ACS Macro Lett 1:589–592. Scholar
  99. 99.
    Jia Y-G, Liu L-Y, Lei B, Li J, Zhu XX (2011) Crown ether cavity-containing copolymers via controlled alternating cyclocopolymerization. Macromolecules 44:6311–6317. Scholar
  100. 100.
    Heravi MM, Hashemi E, Beheshtiha YS, Kamjou K, Toolabi M, Hosseintash N (2014) Solvent-free multicomponent reactions using the novel N-sulfonic acid modified poly(styrene-maleic anhydride) as a solid acid catalyst. J Mol Catal A-Chem 392:173–180. Scholar
  101. 101.
    Heravi MM, Hashemi E, Beheshtiha YS, Ahmadi S, Hosseinnejad T (2014) PdCl2 on modified poly(styrene-co-maleic anhydride): a highly active and recyclable catalyst for the Suzuki–Miyaura and Sonogashira reactions. J Mol Catal A-Chem 394:74–82. Scholar
  102. 102.
    Soer WJ, Ming W, Klumperman B, Koning C, van Benthem R (2006) Surfactant-free artificial latexes from modified styrene–maleic anhydride (SMA) copolymers. Polymer 47:7621–7627. Scholar
  103. 103.
    Baranello MP, Bauer L, Benoit DSW (2014) Poly(styrene-alt-maleic anhydride)-based diblock copolymer micelles exhibit versatile hydrophobic drug loading, drug-dependent release, and internalization by multidrug resistant ovarian cancer cells. Biomacromolecules 15:2629–2641. Scholar
  104. 104.
    Lazzara TD, van de Ven TGM, Whitehead MA (2008) Nanotube self-assembly of a styrene and maleimide alternating copolymer. Macromolecules 41:6747–6751. Scholar
  105. 105.
    Wang Z, Gao M, Sun J, Liang D, Jia X (2013) Photoresponsive dendronized copolymers of styrene and maleic anhydride pendant with poly(amidoamine) dendrons as side groups. Macromolecules 46:1723–1731. Scholar
  106. 106.
    Zhang Z, Hong L, Gao Y, Zhang W (2014) One-pot synthesis of POSS-containing alternating copolymers by RAFT polymerization and their microphase-separated nanostructures. Polym Chem 5:4534–4541. Scholar
  107. 107.
    Zhang Z, Hong L, Li J, Liu F, Cai H, Gao Y, Zhang W (2015) One-pot synthesis of well-defined amphiphilic alternating copolymer brushes based on POSS and their self-assembly in aqueous solution. RSC Adv 5:21580–21587. Scholar
  108. 108.
    Srichan S, Oswald L, Zamfir M, Lutz J-F (2012) Precision polyelectrolytes. Chem Commun 48:1517–1519. Scholar
  109. 109.
    Srichan S, Kayunkid N, Oswald L, Lotz B, Lutz J-F (2014) Synthesis and characterization of sequence-controlled semicrystalline comb copolymers: influence of primary structure on materials properties. Macromolecules 47:1570–1577. Scholar
  110. 110.
    Baradel N, Gok O, Zamfir M, Sanyal A, Lutz J-F (2013) Sequence-controlled polymerization using dendritic macromonomers: precise chain-positioning of bulky functional clusters. Chem Commun 49:7280–7282. Scholar
  111. 111.
    Li Y, Mao M, Matolyak LE, Turner SR (2012) Sterically crowded anionic polyelectrolytes with tunable charge densities based on stilbene-containing copolymers. ACS Macro Lett 1:257–260. Scholar
  112. 112.
    Li Y, Savage AM, Zhou X, Turner SR, Davis RM (2013) Solution properties of stilbene-containing sterically crowded alternating polyanions. J Polym Sci Part B Polym Phys 51:1565–1570. Scholar
  113. 113.
    O’Shea J-P, Solovyeva V, Guo X, Zhao J, Hadjichristidis N, Rodionov VO (2014) Sequence-controlled copolymers of 2,3,4,5-pentafluorostyrene: mechanistic insight and application to organocatalysis. Polym Chem 5:698–701. Scholar
  114. 114.
    Huang J, Zhou X, Lamprou A, Maya F, Svec F, Turner SR (2015) Nanoporous polymers from cross-linked polymer precursors via tert-butyl group deprotection and their carbon dioxide capture properties. Chem Mater 27:7388–7394. Scholar
  115. 115.
    Zhou X, Huang J, Barr KW, Lin Z, Maya F, Abbott LJ, Colina CM, Svec F, Turner SR (2015) Nanoporous hypercrosslinked polymers containing Tg enhancing comonomers. Polymer 59:42–48. Scholar
  116. 116.
    Tang D, Jiang X, Liu H, Li C, Zhao Y (2014) Synthesis and properties of heterografted toothbrush-like copolymers with alternating PEG and PCL grafts and tunable RAFT-generated segments. Polym Chem 5:4679–4692. Scholar
  117. 117.
    Ping J, Gu K, Zhou S, Pan H, Shen Z, Fan X-H (2016) Hierarchically self-assembled amphiphilic alternating copolymer brush containing side-chain cholesteryl units. Macromolecules 49:5993–6000. Scholar
  118. 118.
    Ping J, Pan Y, Pan H, Wu B, Zhou H, Shen Z, Fan X-H (2015) Microphase separation and high ionic conductivity at high temperatures of lithium salt-doped amphiphilic alternating copolymer brush with rigid side chains. Macromolecules 48:8557–8564. Scholar
  119. 119.
    Tsujii A, Namba M, Okamura H, Matsumoto A (2014) Radical alternating copolymerization of twisted 1,3-butadienes with maleic anhydride as a new approach for degradable thermosetting resin. Macromolecules 47:6619–6626. Scholar
  120. 120.
    Kim H, Kang YJ, Jeong ES, Kang S, Kim KT (2012) Glucose-responsive disassembly of polymersomes of sequence-specific boroxole-containing block copolymers under physiologically relevant conditions. ACS Macro Lett 1:1194–1198. Scholar
  121. 121.
    Yang P, Mykhaylyk OO, Jones ER, Armes SP (2016) RAFT dispersion alternating copolymerization of styrene with N-phenylmaleimide: morphology control and application as an aqueous foam stabilizer. Macromolecules 49:6731–6742. Scholar
  122. 122.
    Reches M, Gazit E (2003) Casting metal nanowires within discrete self-assembled peptide nanotubes. Science 300:625–627. Scholar
  123. 123.
    Chen J, Yu C, Shi Z, Yu S, Lu Z, Jiang W, Zhang M, He W, Zhou Y, Yan D (2015) Ultrathin alternating copolymer nanotubes with readily tunable surface functionalities. Angew Chem 127:3692–3696. Scholar
  124. 124.
    Adler-Abramovich L, Gazit E (2014) The physical properties of supramolecular peptide assemblies: from building block association to technological applications. Chem Soc Rev 43:6881–6893. Scholar

Copyright information

© Springer Nature Singapore Pte Ltd. 2020

Authors and Affiliations

  • Ishita Mukherjee
    • 1
  • Krishna Gopal Goswami
    • 1
  • Priyadarsi De
    • 1
    Email author
  1. 1.Department of Chemical SciencesPolymer Research Centre and Centre for Advanced Functional Materials, Indian Institute of Science Education and Research KolkataMohanpur, NadiaIndia

Personalised recommendations