Surface initiated ring-opening polymerization of l-proline N-carboxy anhydride from single and multi walled carbon nanotubes

European Polymer Journal

Volumn 49, Issue 10, 2013, Pages 3095-3103

  Gkikas, Manos ^a   Das, Biswa P ^b   Tsianou, Marina ^b   Iatrou, Hermis ^a   Sakellariou, Georgios ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b State University of New York   (United States)

Author keywords

Carbon nanotubes; Diels Alder cycloaddition; Poly(l proline); Surface initiated ring opening polymerization

Indexed keywords

DIELS-ALDER CYCLOADDITIONS; FUNCTIONALIZED; L-PROLINE; N-CARBOXYANHYDRIDE; PRIMARY AMINES; SURFACE INITIATED POLYMERIZATION; SURFACE-INITIATED; UNIFORM LAYER;

ATOMIC FORCE MICROSCOPY; CARBON NANOTUBES; CYCLOADDITION; GRAFTING (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

POLYMERIZATION;

EID: 84883876173     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2013.07.002     Document Type: Article

References (45)

1. S. Iijima Helical microtubules of graphitic carbón Nature 354 1991 56 58
2. C.A. Cooper, R.J. Young, and M. Halsall Investigation into the deformation of carbon nanotubes and their composites through the use of raman spectroscopy Composites Part A 32A 2001 401 411
3. G. Gao, T. Cagin, and W.A. Goddard Energetics, structure, mechanical and vibrational properties of sigle-walled carbon nanotubes Nanotechnology 9 1998 184 191
4. C. Fabro, H. Ali-Boucetta, T. Da Ros, K. Kostarelos, A. Bianco, and M. Prato Targeting carbon nanotubes against cancer Chem Commun 48 2012 3911 3926
5. D. Pantarotto, R. Singh, D. McCarthy, M. Erhardt, J.P. Briand, and M. Prato Functionalized carbon nanotubes for plasmid DNA gene delivery Angew Chem Int Ed 43 2004 5242 5246
6. C.A. Poland, R. Duffin, I. Kinloch, W.A. Maynard, W.A.H. Wallace, and A. Seaton Carbon nanotubes introduced into the abdominal cavity of mice show asbestos-like pathogenicity in a pilot study Nat Nanotechnol 3 2008 423 428
7. H. Nagai, Y. Okazaki, S.H. Chew, N. Misawa, Y. Yamashita, and S. Akatsuka Diameter and rigidity of multiwalled carbon nanotubes are critical factors in mesothelial injury and carcinogenesis Proc Natl Acad Sci USA 108 2011 E1330 1338
8. G.R. Dieckmann, A.B. Dalton, P.A. Johnson, J. Razal, J. Chen, and G.M. Giordano Controlled assembly of carbon nanotubes by designed amphiphilic peptide helices J Am Chem Soc 125 2003 1770 1777
9. A.B. Dalton, A. Ortiz-Acevedo, V. Zorbas, E. Brunner, W.M. Sampson, and S. Collins Hierarchical self-assembly of peptide-coated carbon nanotubes Adv Funct Mater 14 2004 1147 1151
10. Y. Yao, L. Wenwen, S. Wang, D. Yan, and X. Chen Polypeptide modification of multiwalled carbon nanotubes by a graft-from approach Macromol Rapid Commun 27 2006 2019 2025
11. J. Li, W.D. He, L.P. Yang, X.L. Sun, and Q. Hua Preparation of multi-walled carbon nanotubes grafted with synthetic poly(l-lysine) through surface-initiated ring-opening polymerization Polymer 48 2007 4352 4360
12. H. Tang, and D. Zhang Poly(gamma-benzyl-l-glutamate)-functionalized single-walled carbon nanotubes. Synthesis, characterization and materials properties J Polym Sci Part A Polym Chem 48 2010 2340 2350
13. Y. Zhang, J. Li, Y. Shen, M. Wang, and J. Li Poly-l-lysine functionalization of single-walled carbon nanotubes J Phys Chem B 108 2004 15343 15346
14. C.G. Salzmann, M.A.H. Ward, R.M.J. Jacobs, G. Tobias, and M.L.H. Green Interaction of tyrosine-, tryptophan-, and lysine-containing polypeptides with single-wall carbon nanotubes and its relevance for the rational design of dispersing agents J Phys Chem C 111 2007 18520 18524
15. C.G. Salzmann, G.K.C. Lee, M.A.H. Ward, B.T.T. Chu, and M.L.H. Green Highly hydrophilic and stable polypeptide/single-wall carbon nanotube conjugates J Mater Chem 18 2008 1977 1983
16. G.K.C. Lee, C. Sach, M.L.H. Green, L. Wong, and C.G. Salzmann Mixtures of oppositely charged polypeptides as high-performance dispersing agents for single-wall carbon nanotubes Chem Commun 46 2010 7013 7015
17. C. Li, J. Adamcik, A. Zhang, and R. Mezzenga Twofold pH and temperature stimuli-responsive behaviour in block copolypeptide-decorated single wall carbon nanotubes Chem Commun 47 2011 262 264
18. X. Li, W. Chen, Q. Zhan, L. Dai, L. Sowards, and M. Pender Direct measurements of interactions between polypeptides and carbon nanotubes J Phys Chem B 110 2006 12621 12625
19. D. Baskaran, G. Sakellariou, J.W. Mays, and M.S. Bratcher Grafting reactions of living macroanions with multi-walled carbon nanotubes J Nanosci Nanotechnol 7 2007 1560 1567
20. G. Sakellariou, D. Priftis, and D. Baskaran Surface-initiated polymerization from carbon nanotubes: strategies and perspectives Chem Soc Rev 42 2013 677 704
21. R. Barbey, L. Lavant, D. Paripovic, N. Schuwer, C. Sugnaux, and S. Tugulu Polymer brushes via surface-initiated controlled radical polymerization: synthesis, characterization, properties, and applications Chem Rev 109 2009 5437 5527
22. T. Deming, and A.S. Curtin Chain initiation efficiency in cobalt- and nickel-mediated polypeptide synthesis J Am Chem Soc 122 2000 5710 5717
23. I. Dimitrov, and H. Schlaad Synthesis of nearly monodisperse polystyrene-polypeptide block copolymers via polymerization of N-carboxyanhydrides Chem Commun 23 2003 2944 2945
24. T. Aliferis, H. Iatrou, and N. Hadjichristidis Living polypeptides Biomacromolecules 5 2004 1653 1656
25. W. Vayaboury, O. Giani, H. Cottet, A. Deratani, and F. Schué Living polymerization of alpha-amino acid N-carboxyanhydrides upon decreasing the reaction temperature Macromol Rapid Commun 25 2004 1221 1224
26. H. Lu, and J. Cheng Hexamethyldisilazane-mediated controlled polymerization of α-amino acid N-carboxyanhydrides J Am Chem Soc 129 2007 14114 14115
27. Y. Peng, S. Lai, and C. Lin Preparation of polypeptide via living polymerization of z-lys-nca initiated by platinum complexes Macromolecules 41 2008 3455 3459
28. M. Gkikas, H. Iatrou, N.S. Thomaidis, P. Alexandridis, and N. Hadjichristidis Well-defined homopolypeptides, copolypeptides, and hybrids of poly(l-proline) Biomacromolecules 12 2011 2396 2406
29. S. Sato, Y. Kwon, S. Kamisuki, N. Srivastava, Q. Mao, and Y. Kawazoe Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin J Am Chem Soc 129 2007 873 880
30. Y.A. Fillon, J.P. Anderson, and J. Chmielewski Cell penetrating agents based on a polyproline helix scaffold J Am Chem Soc 127 2005 11798 11803
31. P.S. Arora, A.Z. Ansari, T.P. Best, M. Ptashne, and P.B. Dervan Design of artificial transcriptional activators with rigid poly-l-proline linkers J Am Chem Soc 124 2002 13067 13071
32. L. Crespo, G. Sanclimens, B. Montaner, R. Perez-Tomas, M. Royo, and M. Pons Peptide dendrimers based on polyproline helices J Am Chem Soc 124 2002 8876 8883
33. C.M. Deber, F.A. Bovey, J.P. Carver, and E.R. Blout Nuclear magnetic resonance evidence for cis-peptide bonds in proline oligomers J Am Chem Soc 92 1970 6191 6198
34. A.A. Adzhubei, and M.J.E. Sternberg Left handed polyproline helices commonly occur in globular proteins J Mol Biol 229 1993 472 493
35. B. Bochicchio, and A.M. Tamburro Polyproline II structure in proteins: identification by chiroptical spectroscopies, stability, and functions Chirality 14 2002 782 792
36. I.Z. Steinberg, W.F. Harrington, A. Berger, M. Sela, and E. Katchalski The configurational changes of poly-l-proline in solution J Am Chem Soc 82 1960 5263 5279
37. 13C NMR CP/MAS investigation of the helix stability of solid poly(l-proline)s Macromol Chem 185 1984 1739 1749
38. L. Stryer, and R.P. Haugland Energy transfer: a spectroscopic ruler Proc Natl Acad Sci USA 58 1967 719 725
39. S. Doose, H. Neuweiler, H. Barsch, and M. Sauer Probing polyproline structure and dynamics by photoinduced electron transfer provides evidence for deviations from a regular polyproline type II helix Proc Natl Acad Sci USA 104 2007 17400 17405
40. H. Kricheldorf Polypeptides and 100 years of chemistry of α-amino acid N-carboxyanhydrides Angew Chem Int Ed 45 2006 5752 5784
41. N. Hadjichristidis, H. Iatrou, M. Pitsikalis, and G. Sakellariou Synthesis of well-defined polypeptide-based materials via the ring-opening polymerization of α-amino acid N-carboxyanhydrides Chem Rev 109 2009 5528 5578
42. N. Hadjichristidis, H. Iatrou, M. Pitsikalis, and S. Pispas Anionic polymerization: high vacuum techniques J Polym Sci Part A Polym Chem 38 2000 3211 3234
43. D. Uhrig, and J.W. Mays Experimental techniques in high-vacuum anionic polymerization J Polym Sci Part A Polym Chem 43 2005 6179 6222
44. G. Sakellariou, H. Ji, J.W. Mays, and D. Baskaran Enhanced polymer grafting from multiwalled carbon nanotubes through living anionic surface-initiated polymerization Chem Mater 20 2008 6217 6230
45. G. Sakellariou, H. Ji, J.W. Mays, N. Hadjichristidis, and D. Baskaran Controlled covalent functionalization of multiwalled carbon nanotubes using [4+2] cycloaddition of benzocyclobutenes Chem Mater 19 2007 6370 6372