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Achieving organic nanoparticles with redox-active capabilities: synthesis of gold nanoparticles in water as a proof-of-principle

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Abstract

Herein, we present a unique approach to easily achieve redox-active nanosized organic particles in aqueous environment using a strategy based on ion association between large organic ions, namely tetraphenylborate anions and thiazole orange cations. The anionic tetraphenylborate associates tightly with the cationic redox-active thiazole orange producing a well-defined meta-stable organic nanoscale particle (73 ± 20 nm). These redox-active nanosized organic particles can act as seed sites for metal reductions and as a proof-of-concept, they were used to reduce gold(III) to gold nanoparticles in a neutral, aqueous environment at room temperature.

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References

  • Alvaro M, Cojocaru B, Ismail AA, Petrea N, Ferrer B, Harraz FA, Parvulescu VI, Garcia H (2010) Visible-light photocatalytic activity of gold nanoparticles supported on template-synthesized mesoporous titania for the decontamination of the chemical warfare agent Soman. Appl Catal B-Environ 99(1–2):191–197

    Article  CAS  Google Scholar 

  • Armitage B, Retterer J, Obrien DF (1993) Dimerization of cyanine dyes in water driven by association with hydrophobic borate anions. J Am Chem Soc 115(23):10786–10790

    Article  CAS  Google Scholar 

  • Ban ZH, Bosques CJ, Sasisekharan R (2008) A simple assay to probe disease-associated enzyme activity using glycosaminoglycan-assisted synthesized gold nanoparticles. Org Biomol Chem 6(23):4290–4292

    Article  CAS  Google Scholar 

  • Biver T, Boggioni A, Secco F, Turriani E, Venturini M, Yarnaoluk S (2007) Influence of cyanine dye structure on self-aggregation and interaction with nucleic acids: a kinetic approach to TO and BO binding. Arch Biochem Biophys 465(1):90–100

    Article  CAS  Google Scholar 

  • Boisselier E, Astruc D (2009) Gold nanoparticles in nanomedicine: preparations, imaging, diagnostics, therapies and toxicity. Chem Soc Rev 38(6):1759–1782

    Article  CAS  Google Scholar 

  • Bwambok DK, El-Zahab B, Challa SK, Li M, Chandler L, Baker GA, Warner IM (2009) Near-infrared fluorescent nanoGUMBOS for biomedical imaging. ACS Nano 3(12):3854–3860

    Article  CAS  Google Scholar 

  • Chatterjee S, Gottschalk P, Davis PD, Schuster GB (1988) Electron-transfer reactions in cyanine borate ion-pairs—photopolymerization initiators sensitive to visible-light. J Am Chem Soc 110(7):2326–2328

    Article  CAS  Google Scholar 

  • Daniel MC, Astruc D (2004) Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology. Chem Rev 104(1):293–346

    Article  CAS  Google Scholar 

  • Das S, Bwambok D, Ei-Zahab B, Monk J, de Rooy SL, Challa S, Li M, Hung FR, Baker GA, Warner IM (2010) Nontemplated approach to tuning the spectral properties of cyanine-based fluorescent NanoGUMBOS. Langmuir 26(15):12867–12876

    Article  CAS  Google Scholar 

  • Demers LM, Mirkin CA, Mucic RC, Reynolds RA, Letsinger RL, Elghanian R, Viswanadham G (2000) A fluorescence-based method for determining the surface coverage and hybridization efficiency of thiol-capped oligonucleotides bound to gold thin films and nanoparticles. Anal Chem 72(22):5535–5541

    Article  CAS  Google Scholar 

  • Ghosh SK, Pal T (2007) Interparticle coupling effect on the surface plasmon resonance of gold nanoparticles: from theory to applications. Chem Rev 107(11):4797–4862

    Article  CAS  Google Scholar 

  • Giljohann DA, Seferos DS, Daniel WL, Massich MD, Patel PC, Mirkin CA (2010) Gold nanoparticles for biology and medicine. Angew Chem Inte Ed 49(19):3280–3294

    Article  CAS  Google Scholar 

  • Handley DA (1989) Colloidal gold: principles, methods, and applications. Academic Press, London

    Google Scholar 

  • Hussain ST, Iqbal M, Mazhar M (2009) Size control synthesis of starch capped-gold nanoparticles. J Nanopart Res 11(6):1383–1391

    Article  Google Scholar 

  • Kaeser A, Schenning A (2010) Fluorescent nanoparticles based on self-assembled pi-conjugated systems. Adv Mater 22(28):2985–2997

    Article  CAS  Google Scholar 

  • Kasha M, Rawls HR, Ashraf El-Bayoumi M (1965) The exciton model in molecular spectroscopy. Pure Appl Chem 11(3–4):371–392

    Article  CAS  Google Scholar 

  • Kumar M, George SJ (2011) Green fluorescent organic nanoparticles by self-assembly induced enhanced emission of a naphthalene diimide bolaamphiphile. Nanoscale 3(5):2130–2133

    Article  CAS  Google Scholar 

  • Lau V, Heyne B (2010) Calix[4]arene sulfonate as a template for forming fluorescent thiazole orange H-aggregates. Chem Commun 46(20):3595–3597

    Article  CAS  Google Scholar 

  • Link S, El-Sayed MA (1999) Spectral properties and relaxation dynamics of surface plasmon electronic oscillations in gold and silver nanodots and nanorods. J Phys Chem B 103(40):8410–8426

    Google Scholar 

  • Lovell JF, Jin CS, Huynh E, Jin HL, Kim C, Rubinstein JL, Chan WCW, Cao WG, Wang LV, Zheng G (2011) Porphysome nanovesicles generated by porphyrin bilayers for use as multimodal biophotonic contrast agents. Nat Mater 10(4):324–332

    Article  CAS  Google Scholar 

  • Mann S, Shenton W, Li M, Connolly S, Fitzmaurice D (2000) Biologically programmed nanoparticle assembly. Adv Mater 12(2):147–150

    Article  CAS  Google Scholar 

  • Masuhara H, Nakanishi H, Sasaki K (2003) Single organic nanoparticles. Springer, New York

    Book  Google Scholar 

  • McGilvray KL, Decan MR, Wang DS, Scaiano JC (2006) Facile photochemical synthesis of unprotected aqueous gold nanoparticles. J Am Chem Soc 128(50):15980–15981

    Article  CAS  Google Scholar 

  • Newman JDS, Blanchard GJ (2006) Formation of gold nanoparticles using amine reducing agents. Langmuir 22(13):5882–5887

    Article  CAS  Google Scholar 

  • Ou ZM, Yao H, Kimura K (2007a) Organic nanoparticles of cyanine dye in aqueous solution. Bull Chem Soc Jpn 80(2):295–302

    Article  CAS  Google Scholar 

  • Ou ZM, Yao H, Kimura K (2007b) Preparation and optical properties of organic nanoparticles of porphyrin without self-aggregation. J Photochem Photobiol, A 189(1):7–14

    Article  CAS  Google Scholar 

  • Peng S, McMahon JM, Schatz GC, Gray SK, Sun YG (2010) Reversing the size-dependence of surface plasmon resonances. Proc Natl Acad Sci 107(33):14530–14534

    Article  CAS  Google Scholar 

  • Silva GL, Ediz V, Yaron D, Armitage BA (2007) Experimental and computational investigation of unsymmetrical cyanine dyes: understanding torsionally responsive fluorogenic dyes. J Am Chem Soc 129(17):5710–5718

    Article  CAS  Google Scholar 

  • Yang XQ, Zaitsev A, Sauerwein B, Murphy S, Schuster GB (1992) Penetrated ion-pairs—photochemistry of cyanine dyes within organic borates. J Am Chem Soc 114(2):793–794

    Article  CAS  Google Scholar 

  • Yao H, Ashiba K (2011) Highly fluorescent organic nanoparticles of thiacyanine dye: a synergetic effect of intermolecular H-aggregation and restricted intramolecular rotation. RSC Adv 1(5):834–838

    Article  CAS  Google Scholar 

  • Yao H, Yamashita M, Kimura K (2009) Organic styryl dye nanoparticles: synthesis and unique spectroscopic properties. Langmuir 25(2):1131–1137

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC). The authors would like to thank Mr. W. White for mass spectrometry.

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Authors and Affiliations

  1. Chemistry Department, University of Calgary, 2500 University Drive NW, Calgary, AB, T2N 1N4, Canada

    Sara M. Mooi, Todd C. Sutherland & Belinda Heyne

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  1. Sara M. Mooi
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  2. Todd C. Sutherland
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  3. Belinda Heyne
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Correspondence to Belinda Heyne.

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Mooi, S.M., Sutherland, T.C. & Heyne, B. Achieving organic nanoparticles with redox-active capabilities: synthesis of gold nanoparticles in water as a proof-of-principle. J Nanopart Res 14, 1099 (2012). https://doi.org/10.1007/s11051-012-1099-7

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  • DOI: https://doi.org/10.1007/s11051-012-1099-7

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