Abstract
Dispersion of graphene with high effectiveness is a great challenging task. In this paper, a series of water-soluble polyamine-functionalized perylene bisimide derivatives (HAPBI) were synthesized and further used as the stabilizer of graphene in water. It was found that the number of amine group strongly determined the water solubility of HAPBI and its effectiveness on stabilizing graphene. With triethylenetetramine-functionalized perylene bisimide (HAPBI-3), high concentration of aqueous graphene dispersion up to 1.0 mg mL−1 was obtained at the weight ratio of HAPBI-3 to graphene even down to 1:3, demonstrating its higher efficiency to the common surfactants, polymer, and other perylene bisimide derivatives reported. Moreover, graphene’s electrical conductivity is less impacted compared with polyvinylpyrrolidone (PVP), particularly favoring for its further application. Careful inspection indicated that HAPBI-3 molecules strongly interacted with graphene in a process of de-assembly of their self-aggregates and subsequently irreversible restacking on graphene sheets.
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References
An X et al (2010) Stable aqueous dispersions of noncovalently functionalized graphene from graphite and their multifunctional high-performance applications. Nano Lett 10:4295–4301. https://doi.org/10.1021/nl903557p
Ayán-Varela M et al (2015) Achieving extremely concentrated aqueous dispersions of graphene flakes and catalytically efficient graphene-metal nanoparticle hybrids with flavin mononucleotide as a high-performance stabilizer. ACS Appl Mater Interfaces 7:10293–10307. https://doi.org/10.1021/acsami.5b00910
Backes C, Schmidt CD, Hauke F, Böttcher C, Hirsch A (2009) High population of individualized SWCNTs through the adsorption of water-soluble perylenes. J Am Chem Soc 131:2172–2184. https://doi.org/10.1021/ja805660b
Backes C, Schmidt CD, Rosenlehner K, Hauke F, Coleman JN, Hirsch A (2010) Nanotube surfactant design: the versatility of water-soluble perylene bisimides. Adv Mater 22:788–802. https://doi.org/10.1002/adma.200902525
Backes C, Hauke F, Hirsch A (2011) The potential of perylene bisimide derivatives for the solubilization of carbon nanotubes and graphene. Adv Mater 23:2588–2601. https://doi.org/10.1002/adma.201100300
Duan WH, Wang Q, Collins F (2011) Dispersion of carbon nanotubes with SDS surfactants: a study from a binding energy perspective. Chem Sci 2:1407–1413. https://doi.org/10.1039/c0sc00616e
Englert JM, Röhrl J, Schmidt CD, Graupner R, Hundhausen M, Hauke F, Hirsch A (2009) Soluble graphene: generation of aqueous graphene solutions aided by a perylenebisimide-based bolaamphiphile. Adv Mater 21:4265–4269. https://doi.org/10.1002/adma.200901578
Fernández-Merino MJ et al (2012) Investigating the influence of surfactants on the stabilization of aqueous reduced graphene oxide dispersions and the characteristics of their composite films. Carbon 50:3184–3194. https://doi.org/10.1016/j.carbon.2011.10.039
Georgakilas V et al (2012) Functionalization of graphene: covalent and non-covalent approaches, derivatives and applications. Chem Rev 112:6156–6214. https://doi.org/10.1021/cr3000412
Ghosh A, Rao KV, Voggu R, George SJ (2010) Non-covalent functionalization, solubilization of graphene and single-walled carbon nanotubes with aromatic donor and acceptor molecules. Chem Phys Lett 488:198–201. https://doi.org/10.1016/j.cplett.2010.02.021
Gu L, Liu S, Zhao H, Yu H (2015) Facile preparation of water-dispersible graphene sheets stabilized by carboxylated oligoanilines and their anticorrosion coatings. ACS Appl Mater Interfaces 7:17641–17648. https://doi.org/10.1021/acsami.5b05531
Hsieh AG, Korkut S, Punckt C, Aksay IA (2013) Dispersion stability of functionalized graphene in aqueous sodium dodecyl sulfate solutions. Langmuir 29:14831–14838. https://doi.org/10.1021/la4035326
Johnson DW, Dobson BP, Coleman KS (2015) A manufacturing perspective on graphene dispersions. Curr Opin Colloid Interface Sci 20:367–382. https://doi.org/10.1016/j.cocis.2015.11.004
Kozhemyakina NV, Englert JM, Yang G, Spiecker E, Schmidt CD, Hauke F, Hirsch A (2010) Non-covalent chemistry of graphene: electronic communication with dendronized perylene bisimides. Adv Mater 22:5483–5487. https://doi.org/10.1002/adma.201003206
Lin W et al (2016) Graphene-based fluorescence-quenching-related fermi level elevation and electron-concentration surge. Nano Lett 16:5737–5741. https://doi.org/10.1021/acs.nanolett.6b02430
Liu Z, Robinson JT, Sun X, Dai H (2008) PEGylated nanographene oxide for delivery of water-insoluble cancer drugs. J Am Chem Soc 130:10876–10877. https://doi.org/10.1021/ja803688x
Liu Y, Zhong H, Qin Y, Zhang Y, Liu X, Zhang T (2016) Non-covalent hydrophilization of reduced graphene oxide used as a paclitaxel vehicle. RSC Adv 6:30184–30193. https://doi.org/10.1039/c6ra04349f
Lotya M et al (2009) Liquid phase production of graphene by exfoliation of graphite in surfactant/water solutions. J Am Chem Soc 131:3611–3620. https://doi.org/10.1021/ja807449u
Mo Y, Liu Q, Fan J, Shi P, Min Y, Xu Q (2015) Heterocyclic aramid nanoparticle-assisted graphene exfoliation for fabrication of pristine graphene-based composite paper. J Nanopart Res 17:297. https://doi.org/10.1007/s11051-015-3099-x
Munuera JM et al (2015) High quality, low oxygen content and biocompatible graphene nanosheets obtained by anodic exfoliation of different graphite types. Carbon 94:729–739. https://doi.org/10.1016/j.carbon.2015.07.053
Novoselov KS et al (2004) Electric field effect in atomically thin carbon films. Science 306:666–669. https://doi.org/10.1126/science.1102896
Novoselov KS, Falko VI, Colombo L, Gellert PR, Schwab MG, Kim K (2012) A roadmap for graphene. Nature 490:192–200. https://doi.org/10.1038/nature11458
Pan L et al (2015) Improving thermal and mechanical properties of epoxy composites by using functionalized graphene. RSC Adv 5:60596–60607. https://doi.org/10.1039/c5ra09410k
Parviz D, Das S, Ahmed HST, Irin F, Bhattacharia S, Green MJ (2012) Dispersions of non-covalently functionalized graphene with minimal stabilizer. ACS Nano 6:8857–8867. https://doi.org/10.1021/nn302784m
Perumal S, Park KT, Lee HM, Cheong IW (2016) PVP-b-PEO block copolymers for stable aqueous and ethanolic graphene dispersions. J Colloid Interface Sci 464:25–35. https://doi.org/10.1016/j.jcis.2015.11.014
Qi X et al (2010) Amphiphilic graphene composites. Angew Chem Int Ed 49:9426–9429. https://doi.org/10.1002/anie.201004497
Ren L, Huang S, Zhang C, Wang R, Tjiu WW, Liu T (2012) Functionalization of graphene and grafting of temperature-responsive surfaces from graphene by ATRP “on water”. J Nanopart Res 14:940. https://doi.org/10.1007/s11051-012-0940-3
Roy B, Noguchi T, Yoshihara D, Tsuchiya Y, Dawn A, Shinkai S (2014) Nucleotide sensing with a perylene-based molecular receptor via amplified fluorescence quenching. Org Biomol Chem 12:561–565. https://doi.org/10.1039/c3ob41586d
Salavagione HJ, Gómez MA, Martínez G (2009) Polymeric modification of graphene through esterification of graphite oxide and poly(vinyl alcohol). Macromolecules 42:6331–6334. https://doi.org/10.1021/ma900845w
Salavagione HJ, Ellis G, Segura JL, Gomez R, Morales GM, Martinez G (2011) Flexible film materials from conjugated dye-modified polymer surfactant-induced aqueous graphene dispersions. J Mater Chem 21:16129–16135. https://doi.org/10.1039/c1jm11694k
Schmidt CD, Böttcher C, Hirsch A (2007) Synthesis and aggregation properties of water-soluble newkome-dendronized perylenetetracarboxdiimides. Eur J Org Chem 2007:5497–5505. https://doi.org/10.1002/ejoc.200700567
Sreeprasad TS, Berry V (2013) How do the electrical properties of graphene change with its functionalization? Small 9:341–350. https://doi.org/10.1002/smll.201202196
Stergiou A, Tagmatarchis N (2016) Fluorene–perylene diimide arrays onto graphene sheets for photocatalysis. ACS Appl Mater Interfaces 8:21576–21584. https://doi.org/10.1021/acsami.6b06797
Su Q, Pang S, Alijani V, Li C, Feng X, Müllen K (2009) Composites of graphene with large aromatic molecules. Adv Mater 21:3191–3195. https://doi.org/10.1002/adma.200803808
Sun Z, Masa J, Liu Z, Schuhmann W, Muhler M (2012) Highly concentrated aqueous dispersions of graphene exfoliated by sodium taurodeoxycholate: dispersion behavior and potential application as a catalyst support for the oxygen-reduction reaction. Chem Eur J 18:6972–6978. https://doi.org/10.1002/chem.201103253
Tam-Chang S-W, Seo W, Iverson IK (2004) Synthesis and studies of the properties of a liquid-crystalline quaterrylenebis(dicarboximide) by 1H NMR and UV−vis spectroscopies. J Org Chem 69:2719–2726. https://doi.org/10.1021/jo030342y
Tuntiwechapikul W, Lee JT, Salazar M (2001) Design and synthesis of the G-quadruplex-specific cleaving reagent perylene-EDTA·iron(II). J Am Chem Soc 123:5606–5607. https://doi.org/10.1021/ja0156439
Tuntiwechapikul W, Taka T, Béthencourt M, Makonkawkeyoon L, Randall Lee T (2006) The influence of pH on the G-quadruplex binding selectivity of perylene derivatives. Bioorg Med Chem Lett 16:4120–4126. https://doi.org/10.1016/j.bmcl.2006.04.078
Wajid AS et al (2012) Polymer-stabilized graphene dispersions at high concentrations in organic solvents for composite production. Carbon 50:526–534. https://doi.org/10.1016/j.carbon.2011.09.008
Würthner F (2004) Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem Commun 0:1564–1579. https://doi.org/10.1039/b401630k
Würthner F, Saha-Möller CR, Fimmel B, Ogi S, Leowanawat P, Schmidt D (2016) Perylene bisimide dye assemblies as archetype functional supramolecular materials. Chem Rev 116:962–1052. https://doi.org/10.1021/acs.chemrev.5b00188
Xu LQ et al (2011) Functionalization of reduced graphene oxide nanosheets via stacking interactions with the fluorescent and water-soluble perylene bisimide-containing polymers. Polymer 52:2376–2383. https://doi.org/10.1016/j.polymer.2011.03.054
Xu Z et al (2015) Molecular size, shape, and electric charges: essential for perylene bisimide-based DNA intercalator to localize in cell nuclei and inhibit cancer cell growth. ACS Appl Mater Interfaces 7:9784–9791. https://doi.org/10.1021/acsami.5b01665
Yang X et al (2011) Graphene uniformly decorated with gold nanodots: in situ synthesis, enhanced dispersibility and applications. J Mater Chem 21:8096–8103. https://doi.org/10.1039/c1jm10697j
Yang Y, Rigdon W, Huang X, Li X (2013) Enhancing graphene reinforcing potential in composites by hydrogen passivation induced dispersion. Sci Rep 3:2086. https://doi.org/10.1038/srep02086
Yi M, Shen Z, Ma S, Zhang X (2012) A mixed-solvent strategy for facile and green preparation of graphene by liquid-phase exfoliation of graphite. J Nanopart Res 14:1003. https://doi.org/10.1007/s11051-012-1003-5
Zhang L, Zhang Z, He C, Dai L, Liu J, Wang L (2014) Rationally designed surfactants for few-layered graphene exfoliation: ionic groups attached to electron-deficient π-conjugated unit through alkyl spacers. ACS Nano 8:6663–6670. https://doi.org/10.1021/nn502289w
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This work was financially supported by the National Key Research and Development Program of China (2017YFA0204600) and the National Natural Science Foundation of China (51673047).
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Cui, J., Zhou, S. Polyamine-functionalized perylene bisimide for dispersion of graphene in water with high effectiveness and little impact on electrical conductivity. J Nanopart Res 19, 357 (2017). https://doi.org/10.1007/s11051-017-4047-8
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DOI: https://doi.org/10.1007/s11051-017-4047-8