Abstract
Polynorbornene-functionalized multiwalled carbon nanotubes (MWCNTs) were prepared by a “grafting from” approach, on varying the catalyst-MWCNT spacing to evaluate the influence of the starting catalyst-MWCNT distance on the polymerization efficiency. In particular, 2nd generation Grubbs catalysts and Hoveyda-Grubbs catalysts, both active in the ring opening metathesis polymerization of olefins, were grafted on MWCNTs at 8 to 12 atom spacing from the nanotube surface, and the activity of initiators was tested in the 2-norbornene polymerization. According to our results, initiator performances depend (i) on the length of the arm connecting the catalyst to the MWCNTs, being initiators with longer arms more efficient, and (ii) on the class of Ru catalysts, being Hoveyda-Grubbs catalysts surprisingly more active at room temperatures than 2nd generation Grubbs catalysts. High fractions (80–95 wt%) of polymer covalently bound to the nanotubes in the MWCNT-grafted polynobornene obtained composites were achieved.
Similar content being viewed by others
References
Iijima S (1991) Nature 354:56–8
Coleman JN, Khan U, Gun’ko YK (2006) Adv Mater 18:689–706
Coleman JN, Khan U, Blau WJ, Gun’ko YK (2006) Carbon 44:1624–52
Moniruzzaman M, Winey KI (2006) Macromolecules 39:5194–205
Saligheh O, Forouharshad M, Arasteh R, Eslami-Farasani R, Khajavi R, Yadollah Roudbari B (2013) J Polym Res 20:65–70
Dai H (2002) Surf Sci 500:218–41
Yang B, Pramoda KP, Xu GQ, Goh SH (2007) Adv Funct Mater 17:2062–9
Jeong W, Kessler MR (2008) Chem Mater 20:7060–8
Jeong W, Kessler MR (2009) Carbon 47:2406–12
Byrne MT, Gun’ko YK (2010) Adv Mater 22:1672–88
Zheng J, Zhu Z, Qi J, Zhou Z, Li P, Peng M (2011) J Mater Sci 46:648–58
Tasis D, Tagmatarchis N, Bianco A, Prato M (2006) Chem Rev 106:1105–36
Khan U, Gomes VG, Altarawneh IS (2010) Carbon 48:2925–33
Park SH, Bandaru PR (2010) Polymer 51:5071–7
Zhang C, Tjiu WW, Liu T, Lui WY, Phang IY, Zhang W (2011) J Phys Chem B 115:3392–9
Biewlaski CW, Grubbs RH (2007) Prog Polym Sci 32:1–29
Axel HE, Müller AHE, Matyjaszewski K (2010) Controlled and living polymerizations: from mechanisms to applications. Wiley-VCH, Weinheim
Grubbs RH (2003) Handbook of olefin metathesis. Wiley-VCH, Weinheim
Samojłowicz C, Bieniek M, Grela K (2009) Chem Rev 109:3708–42
Vougioukalakis GC, Grubbs RH (2010) Chem Rev 110:1746–87
Hamad FB, Sun T, Xiao S, Verpoort F (2013) Coord Chem Rev 257:2274–92
Nguyen ST, Grubbs RH, Ziller JW (1993) J Am Chem Soc 115:9858–9
Scholl M, Ding S, Lee CW, Grubbs RH (1999) Org Lett 1:953–6
Garber SB, Kingsbury JS, Gray BL, Hoveyda AH (2000) J Am Chem Soc 122:8168–79
Gessler S, Randl S, Blechert S (2000) Tetrahedron Lett 41:9973–6
Adronov A, Liu Y (2004) Macromolecules 37:4755–60
Costabile C, Grisi F, Siniscalchi G, Longo P, Sarno M, Sannino D, Leone C, Ciambelli P (2011) J Nanosci Nanotechnol 11:10053–62
Bredeau S, Loggioni L, Bertini F, Tritto I, Monteverde F, Alexandre A, Dubois P (2007) Macromol Rapid Commun 28:822–7
Ciambelli P, Sannino D, Sarno M, Fonseca A, Nagy JB (2005) Carbon 43:631–40
Ciambelli P, Sannino D, Sarno M, Leone C, Lafont U (2007) Diamond Relat Mater 16:1144–9
Altavilla C, Sarno M, Ciambelli P (2009) Chem Mater 21:4851–8
Ritter T, Hejl A, Wenzel AG, Funk TW, Grubbs RH (2006) Organometallics 25:5740–5
Vieille-Petit L, Clavier H, Linden A, Blumentritt S, Nolan SP, Dorta R (2010) Organometallics 29:775–88
Vougioukalakis GC, Grubbs RH (2007) Organometallics 26:2469–72
Vougioukalakis GC, Grubbs RH (2008) Chem Eur J 14:7545–56
Grisi F, Mariconda A, Costabile C, Bertolasi V, Longo P (2009) Organometallics 28:4988–95
Costabile C, Mariconda A, Cavallo L, Longo P, Bertolasi V, Ragone F, Grisi F (2011) Chem Eur J 17:8618–29
Perfetto A, Costabile C, Longo P, Bertolasi V, Grisi F (2013) Chem Eur J 19:10492–6
Sanford MS, Ulman M, Grubbs RH (2001) J Am Chem Soc 123:749–50
Sanford MS, Love JA, Grubbs RH (2001) J Am Chem Soc 123:6543–4
Love JA, Sanford MS, Day MW, Grubbs RH (2003) J Am Chem Soc 125:10103–9
Acknowledgments
Financial support from the Ministero dell’Università e della Ricerca Scientifica e Tecnologica is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Additional information
This Article is dedicated to Professor Adolfo Zambelli on the occasion of his 80th birthday.
Rights and permissions
About this article
Cite this article
Costabile, C., Sarno, M., Grisi, F. et al. Influence of the catalyst-nanotube spacing on the synthesis of polymer-functionalized multiwalled carbon nanotubes by “grafting from” approach. J Polym Res 21, 449 (2014). https://doi.org/10.1007/s10965-014-0449-9
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-014-0449-9