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Supramolecular functionalization of single-walled carbon nanotubes with poly(2,5-dihexyl-1,4-phenylene-alt-2-amino-4,6-pyrimidine) and their electrochemical performance

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Abstract

The conjugated polymer poly(2,5-dihexyl-1,4-phenylene-alt-2-amino-4,6-pyrimidine) was synthesized and used in the supramolecular functionalization of single-walled carbon nanotubes (SWNTs). It was found that this polymer can form strong supramolecular polymer–nanotube assembly and produce a stable composite in solution. The resulting polymerized nanotubes were analyzed by UV–Vis absorption and emission spectroscopy, thermogravimetry, transmission electron microscopy and scanning electron microscopy. It was found that the noncovalent functionalization did not damage the nanotube structure. The polymer content in the polymer–nanotube composite could be calculated to be 41% by thermogravimetry analysis. The composite exhibited certain solubility in dimethylacetamide (DMAc), where the solubility in the absence of excess free polymer solution is 78.7 mg L−1. The composite exhibited a conductivity of 0.005 S cm−1 and the anodic and cathodic peaks were observed at 0.47 and 0.37 V. Galvanostatical charge/discharge tests give good cycling behavior of maintaining a stable capacitance value of 66.7 F g−1 over 1000 cycles at a current load of 1 mA cm−2 without distinct drop.

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References

  1. D. Tasis, N. Tagmatarchis, A. Bianco, and M. Prato: Chemistry of carbon nanotubes. Chem. Rev. 106, 1105 (2006).

    Article  CAS  Google Scholar 

  2. T. Casagrande, P. Imin, F. Cheng, G.A. Botton, I. Zhitomirsky, and A. Adronov: Synthesis and electrophoretic deposition of single-walled carbon nanotube complexes with a conjugated polyelectrolyte. Chem. Mater. 22, 2741 (2010).

    Article  CAS  Google Scholar 

  3. A.B. Kaiser and V. Skákalová: Electronic conduction in polymers, carbon nanotubes and graphene. Chem. Soc. Rev. 40, 3786 (2011).

    Article  CAS  Google Scholar 

  4. P. Imin, M. Imit, and A. Adronov: Supramolecular functionalization of single-walled carbon nanotubes (SWNTs) with a photoisomerizable conjugated polymer. Macromolecules 45, 5045 (2012).

    Article  CAS  Google Scholar 

  5. F. Wang, H.W. Gu, and T.M. Swager: Carbon nanotube/polythiophene chemiresistive sensors for chemical warfare agents. J. Am. Chem. Soc. 130, 5392 (2008).

    Article  CAS  Google Scholar 

  6. M.M. Rahman, A. Umar, and K. Sawada: Development of amperometric glucose biosensor based on glucose oxidase co-immobilized with multi-walled carbon nanotubes at low potential. Sens. Actuators, B 137, 327 (2009).

    Article  Google Scholar 

  7. X. Pang, P. Imin, I. Zhitomirsky, and A. Adronov: Amperometric detection of glucose using a conjugated polyelectrolyte complex with single-walled carbon nanotubes. Macromolecules 43, 10376 (2010).

    Article  CAS  Google Scholar 

  8. C. Rutherglen and P. Burke: Carbon nanotube radio. Nano Lett. 7, 3296 (2007).

    Article  CAS  Google Scholar 

  9. T. Schuettfort, A. Nish, and R. Nicholas: Observation of a type II heterojunction in a highly ordered polymer–carbon nanotube nanohybrid structure. Nano Lett. 9, 3871 (2009).

    Article  CAS  Google Scholar 

  10. P. Francisco and E.R. Daniel: Water solubilization of single-walled carbon nanotubes by functionalization with glucosamine. Nano Lett. 2, 369 (2002).

    Article  Google Scholar 

  11. N. Grossiord, J. Loos, O. Regev, and C.E. Koning: Toolbox for dispersing carbon nanotubes into polymers to get conductive nanocomposites. Chem. Mater. 18, 1089 (2006).

    Article  CAS  Google Scholar 

  12. P. Imin, M. Imit, and A. Adronov: Supramolecular functionalization of single-walled carbon nanotubes (SWNTs) with dithieno[3,2-b:20,30-d]pyrrole (DTP) containing conjugate polymers. Macromolecules 44, 9138 (2011).

    Article  CAS  Google Scholar 

  13. Z.L. Yao, N. Braidy, A.B. Gianluigi, and A. Adronov: Polymerization from the surface of single-walled carbon nanotubes − preparation and characterization of nanocomposites. J. Am. Chem. Soc. 125, 16015 (2003).

    Article  CAS  Google Scholar 

  14. S. Banerjee, T.B. Hemraj, and S.S. Wong: Covalent surface chemistry of single-walled carbon nanotubes. Adv.Mater. 17, 17 (2005).

    Article  CAS  Google Scholar 

  15. C.M. Homenick, G. Lawson, and A. Adronov: Polymer grafting of carbon nanotubes using living free-radical polymerization. Polym. Rev. 47, 265 (2007).

    Article  CAS  Google Scholar 

  16. P. Imin, F.Y. Cheng, and A. Adronov: Supramolecular complexes of single walled carbon nanotubes with conjugated polymers. Polym. Chem. 2, 411 (2011).

    Article  CAS  Google Scholar 

  17. F. Cheng, P. Imin, C. Maunders, G. Botton, and A. Adronov: Soluble, discrete supramolecular complexes of single-walled carbon nanotubes with fluorene-based conjugated polymers. Macromolecules 41, 2304 (2008).

    Article  CAS  Google Scholar 

  18. A. Nish, J.Y. Hwang, J. Doig, and R.J. Nicholas: Fluorescence spectroscopy of electrochemically self-assembled ZnSe and Mn:ZnSe nanowires. Nanotechnology 19, 195601 (2008).

    Article  Google Scholar 

  19. I. Singh, P.K. Bhatnagar, P.C. Mathur, I. Kaur, L.M. Bharadwaj, and R. Pandey: Optical and electrical characterization of conducting polymer-single walled carbon nanotube composite films. Carbon 46, 1141 (2008).

    Article  CAS  Google Scholar 

  20. A. Ikeda, K. Nobusawa, T. Hamano, and J-i. Kikuchi: Single-walled carbon nanotubes template the one-dimensional ordering of a polythiophene derivative. Org. Lett. 8, 5489 (2006).

    Article  CAS  Google Scholar 

  21. Y. Zhang, R. Jamal, W. Shao, and T. Abdiryim: The mechanochemical synthesis of poly(3′,4′-ethylenedioxy-2,2′:5′,2″-terthiophene)/graphene nanoplatelet composites and the electrochemical performance. Electrochim. Acta 113, 382 (2013).

    Article  CAS  Google Scholar 

  22. M.J. O’Connell, S. Sivaram, and S.K. Doorn: Near-infrared resonance Raman excitation profile studies of single-walled carbon nanotube intertube interactions: A direct comparison of bundled and individually dispersed HiPco nanotubes. Phys. Rev. B 69, 235415 (2004).

    Article  Google Scholar 

  23. H. Kawamoto, T. Uchida, K. Kojima, and M. Tachibana: The feature of the Breit-Wigner-Fano Raman line in DNA-wrapped single-wall carbon nanotubes. J. Appl. Phys. 99, 094309 (2006).

    Article  Google Scholar 

  24. N.J. Alley, K.S. Liao, E. Andreoli, S. Dias, E.P. Dillon, A.W. Orbaek, A.R. Barron, H.J. Byrne, and S.A. Curran: Effect of carbon nanotube-fullerene hybrid additive on P3HT: PCBM bulk-heterojunction organic photovoltaics. Synth. Met. 162, 95 (2012).

    Article  CAS  Google Scholar 

  25. V. Balachandran, A. Lakshmi, and A. Janaki: Vibrational spectroscopic studies and natural bond orbital analysis of 4,6-dichloro-2-(methylthio)pyrimidine based on density functional theory. Spectrochim. Acta, Part A 81, 1 (2011).

    Article  CAS  Google Scholar 

  26. S. Bibekananda, C. Ajeong, and W.P. Yung: Highly conducting electrospun polyaniline- polyethylene oxide nanofibrous membranes filled with single-walled carbon nanotubes. Synth. Met. 160, 984 (2010).

    Article  Google Scholar 

  27. M. Panhuis, M.L. Kane, S. Moulton, P.C. Innis, and G.G. Wallace: Stabilization of single-wall carbon nanotubes in fully sulfonated polyaniline. J. Nanosci. Nanotechnol. 4, 976 (2004).

    Article  CAS  Google Scholar 

  28. J.G. Kerry, E.M. Simon, and G.W. Gordon: Incorporation of carbon nanotubes into the biomedical polymer poly(styrene-β-isobutylene-β-styrene). Carbon 45, 402 (2007).

    Article  Google Scholar 

  29. A. Dalton, C. Stephan, J. Coleman, B. McCarthy, P. Ajayan, S. Lefrant, P. Bernier, W. Blau, and H. Byrne: Selective interaction of a semiconjugated organic polymer with single-wall nanotubes. J. Phys. Chem. B 104, 10012 (2000).

    Article  CAS  Google Scholar 

  30. G.R. Dieckmann, A.B. Dalton, P.A. Johnson, J. Razal, J. Chen, G.M. Giordano, E. Muñoz, I.H. Musselman, R.H. Baughman, and R.K. Draper: Controlled assembly of carbon nanotubes by designed amphiphilic peptide helices. J. Am. Chem. Soc. 125, 1770 (2003).

    Article  CAS  Google Scholar 

  31. Q. Zhao, J.R. Wood, and H.D. Wagner: Stress fields around defects and fibers in a polymer using carbon nanotubes as sensors. Appl. Phys. Lett. 78, 1748 (2001).

    Article  CAS  Google Scholar 

  32. Q. Zhao and H.D. Wagner: Two-dimensional strain mapping in model fiber-polymer composites using nanotube Raman sensing. Composites, Part A 34, 1219 (2003).

    Article  Google Scholar 

  33. Q. Zhao, R. Tannenbaum, and K.I. Jacob: Carbon nanotubes as Raman sensors of vulcanization in natural rubber. Carbon 44, 1740 (2006).

    Article  CAS  Google Scholar 

  34. X. Mamtimin, R. Matsidik, and I. Nurulla: New soluble rigid rod copolymers comprising alternating 2-amino-pyrimidine and phenylene repeat units: Syntheses, characterization, optical and electrochemical properties. Polymer 51, 437 (2010).

    Article  CAS  Google Scholar 

  35. T. Abdiryim, R. Jamal, C. Zhao, T. Awut, and I. Nurulla: Structure and properties of solid-state synthesized poly(3′,4′-ethylenedioxy-2, 2′:5′,2″-terthiophene). Synth. Met. 160, 325 (2010).

    Article  CAS  Google Scholar 

  36. U. Aminam, J. Ruxangul, R. Adalet, T. Awut, I. Nurulla, and T. Abdiryim: Solid-state synthesis and characterization of polyaniline/multi-walled carbon nanotubes composite. Synth. Met. 161, 2097 (2011).

    Article  Google Scholar 

  37. T. Fujigaya, M. Okamoto, and N. Nakashima: Design of an assembly of pyridine-containing polybenzimidazole, carbon nanotubes and Pt nanoparticles for a fuel cell electrocatalyst with a high electrochemically active surface area. Carbon 47, 3227 (2009).

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors gratefully acknowledge the support from the Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education and Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Natural Science Foundation of Xinjiang University and National Natural Science Foundation of China (Grant Nos. 21164012, 51363020, XJDX0908-2010-07, BS110116).

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Sidik, S., Mamtimin, X. Supramolecular functionalization of single-walled carbon nanotubes with poly(2,5-dihexyl-1,4-phenylene-alt-2-amino-4,6-pyrimidine) and their electrochemical performance. Journal of Materials Research 29, 2634–2643 (2014). https://doi.org/10.1557/jmr.2014.318

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  • DOI: https://doi.org/10.1557/jmr.2014.318

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