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A fast and facile synthetic route toward the preparation of nanoparticles of polythiophene and its derivatives

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Abstract

A novel photochemical water-based approach for the preparation of nanoparticles of polymerized thiophene (Th), thiophene methanol (ThM), or their mixtures (Th-co/or-ThM) was developed. The influence of 3-[(2-acryloyloxy)methyl] thiophene (ATh) as cross-link agent on the stability of the nanoparticles and on their performances was investigated. The occurrence of a polymerization process was confirmed by Fourier transform infrared (FT-IR), UV and fluorescence emission spectroscopies. Nanoparticles with very narrow size distribution (0.0092–0.105 ATh cross-linked, 0.0635–0.272 uncross-linked) and ideal spherical shape (radius 35–47 nm ATh cross-linked, 49–109 nm uncross-linked) were obtained whatever the reaction composition. The size of the particles was found to depend strongly on the level of ATh-stabilization and to diminish upon increase of the ATh content. In contrast, in the same order, their thermal stability shifted toward higher temperatures. Thermal decomposition of the nanoparticles led to formation of carbon-nanoobjects, as observed by transmission electron microscopy, FT-IR, and RAMAN spectroscopies. The re-dispersibility of the dry Th-co/or-ThM nanoparticles in some conventional monomers and solvents has been estimated.

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References

  • Caseri W (2000) Nanocomposites of polymers and metals or semiconductors: historical background and optical properties. Macromol Rapid Commun 21:705–722

    Article  CAS  Google Scholar 

  • Christian GD, O’Reilly JE (2003) Instrumental analysis, 2nd edn. Sv. Kliment Ohridski, Sofia, pp 189–202

    Google Scholar 

  • Evans CH, Scaiano JC (1990) Photochemical generation of radical cations from terthienyl and related thiophenes: kinetic behaviour and magnetic field effects on radical-ion pairs in micellar solution. J Am Chem Soc 112:2694–2701

    Article  CAS  Google Scholar 

  • Evans C, Scaiano JC, Mac Eachern A, Arnaso JT, Morand P, Hollebone B, Leitch LC, Philogene BJR (1986) Photochemistry of the botanical phototoxin, α-terthienyl and some related compounds. Photochem Photobiol 44(4):441–451

    Article  CAS  Google Scholar 

  • Fujitsuka M, Sato T, Segawa H, Shimidzu T (1995) Photochemical polymerization of oligothiophene and dithienothiophene. Synth Metals 69:309–310

    Article  CAS  Google Scholar 

  • Guner Y, Toppare L, Hepuzer Y, Yagci Y (2004) Conducting graft copolymers of pyrrole and thiophene with random copolymers of methyl methacrylate and 3-methylthienyl methacrylate. Eur Polym J 40:1799–1806

    Article  CAS  Google Scholar 

  • Huisman CL, Huijser A, Donker H, Schoonman J, Goossens A (2005) UV polymerization of oligothiophenes and their application in nanostructured heterojunction solar cells. Macromolecules 37:5557–5564

    Article  Google Scholar 

  • Imit M, Yamamoto T, Imin P (2005) Photochemical reactions of poly(3-thiophene-2,5-diyl) with chloroform. J Zhejiang Univ SCI 6B(8):722–724

    Article  CAS  Google Scholar 

  • Jang J, Li XL, Oh JH (2004) Facile fabrication of polymer and carbon nanocapsules using polypyrrole core/shell nanomaterials. Chem Commun 7:794–795

    Article  Google Scholar 

  • Kock TJJM, De Ruiter B (1996) A radiation-crosslinkable thiophene copolymers. Synth Metals 79:215–218

    Article  CAS  Google Scholar 

  • Lee JM, Lee SJ, Jung YJ, Kim JH (2008) Fabrication of nao-structured polythiophene nanoparticles in aqueous dispersion. Curr Appl Phys 8(6):659–663

    Article  Google Scholar 

  • Li XG, Li J, Meng QK, Huang MR (2009a) Interfacial synthesis and widely controllable conductivitity of polythiophene microparticles. J Phys Chem 113(29):9718–9727

    CAS  Google Scholar 

  • Li XG, Li J, Huang MR (2009b) Facile optimal synthesis of inherently electroconductive polythiophene nanoparticles. Chem A Eur J 15(26):6446–6455

    Article  CAS  Google Scholar 

  • Liu G, Natarjan S, Kim SH (2005) Photochemical production of oligothiophene and polythiophene micropatterns from 2,5-diidothiophene on Au in UHV. Surf Sci 592:L305–L309

    Article  CAS  Google Scholar 

  • Moorlag C, Sih BC, Stott TL, Wolf MO (2005) Metal-containing conjugated materials: oligomers, polymers and nanomaterials. J Mater Chem 15:2433–2436

    Article  CAS  Google Scholar 

  • Natarajan S, Kim SH (2006a) Photochemical conversion of 2,5-diiodothiophene condensed on substrates to oligothiophene and polythiophene thin films and micro-patterns. Thin Solid Films 496:606–611

    Article  CAS  Google Scholar 

  • Natarajan S, Kim SH (2006b) Synthesis-in-place of highly-conjugated oligothiophene micropatterns via photo-activated Ulmann coupling on copper surface. Chem Commun 2006:729–731

    Article  Google Scholar 

  • Natarajan S, Kim SH (2007) Photochemical oligomeriztion pathways in 2,5-diidothiophene film. J Photochem Photobiol A 188:342–345

    Article  CAS  Google Scholar 

  • Oh SG, Im SS (2002) Electrocunductive polymer nanoparticles: preparation and characterization of PANI and PEDOT nanoparticles. Curr Appl Phys 2:273–277

    Article  Google Scholar 

  • Ong BS, Wu Y, Liu P, Gardner S (2005) Structurally ordered polythiophene nanoparticles for high-performance organic thin-films transistors. Adv Mater 17:1141–1144

    Article  CAS  Google Scholar 

  • Piletsky SA, Piletska EV, Karim K, Davis F, Higson SPJ, Turner APF (2004) Photochemical polymerization of thiophene derivatives in aqueous solution. Chem Commun 2004:2222–2223

    Article  Google Scholar 

  • Qiao WM, Song J, Lim SY, Hong SH, Yoon SH, Mochida I, Imaoka T (2006) Carbon nanospheres produced in an arc-discharge process. Carbon 44(1):187–190

    Article  CAS  Google Scholar 

  • Rowley NM, Mortimer RJ (2002) New electrochromic materials. Sci Progr 85(3):243–262

    Article  CAS  Google Scholar 

  • Si P, Chi Z, Ulstrup J, Moller PJ, Mortensen J (2007) Functional polythiophene nanoparticles: size-controlled electropolymerization and ion selective response. J Am Chem Soc 129:3888–3896

    Article  CAS  Google Scholar 

  • Toshima N, Hara S (1995) Direct synthesis of conducting polymers from simple monomers. Prog Polym Sci 20:155–183

    Article  CAS  Google Scholar 

  • Vu QT, Pavlik M, Hebestreit N, Rammelt U, Plieth W, Pfleger J (2005) Nanocomposites based on titanium dioxide and polythiophene: structure and properties. React Funct Polym 65:69–77

    Article  CAS  Google Scholar 

  • Wang Z, Wang Y, Xu D, Kong ESW, Zhang Y (2010) Facile synthesis of dispersible spherical polythiophene nanoparticles by copper(II) catalysed oxidative polymerization in aqueous medium. Synth Metals 160:921–926

    Article  CAS  Google Scholar 

  • Wintgens V, Valat P, Garnier F (1994) Photochemical generation of radical cations from thiophene oligomers. J Phys Chem 98:228–232

    Article  CAS  Google Scholar 

  • Xia C, Fan X, Locklin J, Advincula RC, Gies A, Nonidez W (2004) Characterization, supramolecular assembly and nanostructures of thiophene dendrimers. J Am Chem Soc 126:8735–8743

    Article  CAS  Google Scholar 

  • Yagci Y, Yilmaz F, Kiralp S, Toppare L (2005) Photoinduced polymerization of thiophene using iodonium salt. Macromol Chem Phys 206:1178–1182

    Article  CAS  Google Scholar 

  • Yamamoto T (2002) π-Conjugated polymers with electronic and optical functionalities: preparation by organometallic polycondensation, properties and application. Macromol Rapid Commun 23:583–606

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Center for Education and Research on Macromolecules (CERM), University of Liege, B6 Sart-Tilman, 4000, Liege, Belgium

    Dimitriya Bozukova, Robert Jérôme & Christine Jérôme

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  1. Dimitriya Bozukova
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  2. Robert Jérôme
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  3. Christine Jérôme
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Correspondence to Dimitriya Bozukova.

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Bozukova, D., Jérôme, R. & Jérôme, C. A fast and facile synthetic route toward the preparation of nanoparticles of polythiophene and its derivatives. J Nanopart Res 15, 1583 (2013). https://doi.org/10.1007/s11051-013-1583-8

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  • DOI: https://doi.org/10.1007/s11051-013-1583-8

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