Bio-adenine-bridged molecular design approach toward non-covalent functionalized graphene by liquid-phase exfoliation
Source abstract
Abstract
Here, the supramolecular interaction between nucleobase adenine and graphene was strengthened by a novel chemical molecular designing strategy. Based on this approach, the adenine-bridged aromatic phthalonitrile (AAPN) was prepared as stabilizer toward liquid-phase exfoliation for non-covalent functionalized graphene (AAPN-G). A series of experiments were carried out to verify the strong supramolecular interaction between AAPN and graphene. The feasibility of multifunctional application of the AAPN was briefly demonstrated. This work constitutes a feasible strategy in the preparation and functionalization of graphene that could be extended to some other (bio)molecules toward realization of designing multifunctional materials.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Graphene research and applications · Graphene and Nanomaterials Applications · Molecular Junctions and Nanostructures
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (53)
Show source-provided references
1. Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV et al (2004) Electric field effect in atomically thin carbon films. Science 306:666–66910.1126/science.1102896 ↗
2. Lin S, Ju S, Shi G, Zhang J, He Y, Jiang D (2019) Ultrathin nitrogen-doping graphene films for flexible and stretchable EMI shielding materials. J Mater Sci 54:7165–7179. https://doi.org/10.1007/s10853-019-03372-410.1007/s10853-019-03372-4 ↗
3. Liu J, Ma Q, Huang Z, Liu G, Zhang H (2019) Recent progress in graphene-based noble-metal nanocomposites for electrocatalytic applications. Adv Mater 31:180069610.1002/adma.201800696 ↗
4. Kumar A, Sharma K, Dixit AR (2019) A review of the mechanical and thermal properties of graphene and its hybrid polymer nanocomposites for structural applications. J Mater Sci 54:5992–6026. https://doi.org/10.1007/s10853-018-03244-310.1007/s10853-018-03244-3 ↗
5. Peng P, Li L, He P, Zhu Y, Fu J, Huang Y et al (2019) One-step selective laser patterning of copper/graphene flexible electrodes. Nanotechnology 30:18530110.1088/1361-6528/aafe4c ↗
6. Li T, Liu P, Gao Y, Diao S, Wang X, Yang B et al (2019) High electrochemical performance of supercapacitor electrode with para-aminophenyl graphene/polyaniline cross-linking nanocomposites. Mater Lett 244:13–1710.1016/j.matlet.2019.02.046 ↗
7. Kuilla T, Bhadra S, Yao D, Kim NH, Bose S, Lee JH (2010) Recent advances in graphene based polymer composites. Prog Polym Sci 35:1350–137510.1016/j.progpolymsci.2010.07.005 ↗
8. Liu Y, Li J, Li W, Li Y, Chen Q, Zhan F (2015) Nitrogen-doped graphene aerogel-supported spinel CoMn2O4 nanoparticles as an efficient catalyst for oxygen reduction reaction. J Power Sources 299:492–50010.1016/j.jpowsour.2015.09.042 ↗
9. Si Y, Samulski ET (2008) Synthesis of water soluble graphene. Nano Lett 8:1679–168210.1021/nl080604h ↗
10. Rouf TB, Kokini JL (2019) Biodegradable biopolymer–graphene nanocomposites. J Mater Sci 51:9915–9945. https://doi.org/10.1007/s10853-016-0238-410.1007/s10853-016-0238-4 ↗
11. Khodadadi Dizaji A, Mortaheb HR, Mokhtarani B (2016) Noncovalently functionalized graphene oxide/graphene with imidazolium-based ionic liquids for adsorptive removal of dibenzothiophene from model fuel. J Mater Sci 51:10092–10103. https://doi.org/10.1007/s10853-016-0237-510.1007/s10853-016-0237-5 ↗
12. Tahara K, Ishikawa T, Hirsch BE, Kubo Y, Brown A, Eyley S et al (2018) Self-assembled monolayers as templates for linearly nanopatterned covalent chemical functionalization of graphite and graphene surfaces. ACS Nano 12:11520–1152810.1021/acsnano.8b06681 ↗
13. Lin P, Meng L, Huang Y, Liu L, Fan D (2015) Simultaneously functionalization and reduction of graphene oxide containing isocyanate groups. Appl Surf Sci 324:784–79010.1016/j.apsusc.2014.11.038 ↗
14. Georgakilas V, Bourlinos AB, Zboril R, Steriotis TA, Dallas P, Stubos AK et al (2010) Organic functionalisation of graphenes. Chem Commun 46(10):1766–176810.1039/b922081j ↗
15. Georgakilas V, Tiwari JN, Kemp KC, Perman JA, Bourlinos AB, Kim KS et al (2016) Noncovalent functionalization of graphene and graphene oxide for energy materials, biosensing, catalytic, and biomedical applications. Chem Rev 116:5464–551910.1021/acs.chemrev.5b00620 ↗
16. Yu G, Xue M, Zhang Z, Li J, Han C, Huang F (2012) A water-soluble pillar[6]arene: synthesis, host-guest chemistry, and its application in dispersion of multiwalled carbon nanotubes in water. J Am Chem Soc 134:13248–1325110.1021/ja306399f ↗
17. Yu G, Li J, Yu W, Han C, Mao Z, Gao C et al (2013) Carbon nanotube/biocompatible bola-amphiphile supramolecular biohybrid materials: preparation and their application in bacterial cell agglutination. Adv Mater 25:6373–637910.1002/adma.201302942 ↗
18. Yang J, Yu G, Xia D, Huang F (2014) A pillar[6]arene-based UV-responsive supra-amphiphile: synthesis, self-assembly, and application in dispersion of multiwalled carbon nanotubes in water. Chem Commun 50:3993–399510.1039/c4cc00590b ↗
19. Tang Z, Lei Y, Guo B, Zhang L, Jia D (2012) The use of rhodamine B-decorated graphene as a reinforcement in polyvinyl alcohol composites. Polymer 53:673–68010.1016/j.polymer.2011.11.056 ↗
20. Kim T, Lee H, Kim J, Suh KS (2010) Synthesis of phase transferable graphene sheets using ionic liquid polymers. ACS Nano 4:1612–161810.1021/nn901525e ↗
21. Kodali VK, Scrimgeour J, Kim S, Hankinson JH, Carroll KM, de Heer WA et al (2011) Nonperturbative chemical modification of graphene for protein micropatterning. Langmuir 27:863–86510.1021/la1033178 ↗
22. Paredes JI, Villarrodil S (2016) Biomolecule-assisted exfoliation and dispersion of graphene and other two-dimensional materials: a review of recent progress and applications. Nanoscale 8:15389–1541310.1039/C6NR02039A ↗
23. Cheng G, Han X, Hao S, Nisic M, Zheng S (2018) In situ caging of biomolecules in graphene hybrids for light modulated bioactivity. ACS Appl Mater Interfaces 10:3361–337110.1021/acsami.7b17544 ↗
24. Liu F, Choi JY, Seo TS (2010) DNA mediated water-dispersible graphene fabrication and gold nanoparticle-graphene hybrid. Chem Commun 46:2844–284610.1039/b923656b ↗
25. Sharifi F, Bauld R, Ahmed MS, Fanchini G (2012) Transparent and conducting graphene-RNA-based nanocomposites. Small 8:699–70610.1002/smll.201101537 ↗
26. Ayán-Varela M, Pérez-Vidal Ó, Paredes JI, Munuera JM, Villar-Rodil S, Díaz-González M et al (2017) Aqueous exfoliation of transition metal dichalcogenides assisted by DNA/RNA nucleotides: catalytically active and biocompatible nanosheets stabilized by acid-base interactions. ACS Appl Mater Interfaces 9:2835–284510.1021/acsami.6b13619 ↗
27. Sano T, Nishio Y, Hamada Y, Takahashi H, Usuki T, Shibata K (2000) Design of conjugated molecular materials for optoelectronics. J Mater Chem 10:157–16110.1039/a903239h ↗
28. Jiang H (2010) Organic ambipolar conjugated molecules for electronics: synthesis and structure-property relationships. Macromol Rapid Commun 31:2007–203410.1002/marc.201000040 ↗
29. Cheng Y, Qi Y, Tang Y, Zheng C, Wan Y, Huang W et al (2016) Controlling intramolecular conformation through nonbonding interaction for soft-conjugated materials: molecular design and optoelectronic properties. J Phys Chem Lett 7:3609–361510.1021/acs.jpclett.6b01695 ↗
30. Hernandez Y, Nicolosi V, Lotya M, Blighe FM, Sun Z, De S et al (2008) High-yield production of graphene by liquid-phase exfoliation of graphite. Nat Nanotechnol 3:563–56810.1038/nnano.2008.215 ↗
31. Hu J, Wang Z, Lu Z, Chen C, Shi M, Wang J et al (2017) Bio-based adenine-containing high performance polyimide. Polymer 119:59–6510.1016/j.polymer.2017.05.012 ↗
32. Hu J, Chen C, Yang F, He B, Lu Z, Li R et al (2018) High performance polyimides containing bio-molecule adenine building block from DNA. Polymer 146(20):407–41610.1016/j.polymer.2018.05.006 ↗
33. Hu J, Li R, Chen C, Lu Z, Yang G, Zeng K (2018) New insights into mechanism of negative in-plane CTE based on bio-based adenine-containing polyimide film. Polymer 146(20):133–14110.1016/j.polymer.2018.05.001 ↗
34. Lu Z, Hu JH, Chen C, Peng WF, Liu ZZ, Liu Y et al (2018) Preparation and characterization of adenine-based polyimide/nano-silica hybrid films. Eur Polymer J 102:209–21810.1016/j.eurpolymj.2018.03.019 ↗
35. Chen C, Hu J, Wang Z, Ma J, Cheng K, Lv J et al (2018) Synthesis and characterization of novel polyamides containing purine moiety. Polym Plast Technol Eng 57(13):1325–133310.1080/03602559.2017.1381247 ↗
36. Pu F, Ren J, Qu X (2018) Nucleobases, nucleosides, and nucleotides: versatile biomolecules for generating functional nanomaterials. Chem Soc Rev 47:1285–130610.1039/C7CS00673J ↗
37. Li C, Zhou C, Lv J, Liang B, Li R, Liu Y et al (2019) Bio-molecule adenine building block effectively enhances electromagnetic interference shielding performance of polyimide-derived carbon foam. Carbon 149:190–20210.1016/j.carbon.2019.04.012 ↗
38. Peng W, Yao F, Hu J, Liu Y, Lu Z, Liu Y et al (2018) Renewable protein-based monomer for thermosets: a case study on phthalonitrile resin. Green Chem 20:5158–516810.1039/C8GC01824C ↗
39. Laskoski M, Clarke JS, Neal A, Harvey BG, Ricks-Laskoski HL, Hervey WJ et al (2016) Sustainable high-temperature phthalonitrile resins derived from resveratrol and dihydroresveratrol. ChemistrySelect 1:3423–342710.1002/slct.201600304 ↗
40. Zeng K, Zhou K, Zhou S, Hong H, Zhou H, Wang Y et al (2009) Studies on self-promoted cure behaviors of hydroxy-containing phthalonitrile model compounds. Eur Polym J 45:1328–133510.1016/j.eurpolymj.2008.12.036 ↗
41. Wu D, Zhao Y, Zeng K, Yang G (2012) A novel benzimidazole-containing phthalonitrile monomer with unique polymerization behavior. J Polym Sci A Polym Chem 50:4977–498210.1002/pola.26331 ↗
42. Anbarasan PM, Vasudevan K, Kumar PS, Prakasam A, Geetha M, Lalithambigai K (2012) Structural and spectral properties of 4-phenoxyphthalonitrile dye sensitizer for solar cell applications. Bull Mater Sci 35:265–27510.1007/s12034-012-0281-y ↗
43. Dong S, Xu M, Wei J, Yang X, Liu X (2014) The preparation and wide frequency microwave absorbing properties of tri-substituted-bisphthalonitrile/Fe3O4 magnetic hybrid microspheres. J Magn Magn Mater 349:15–2010.1016/j.jmmm.2013.08.038 ↗
44. Liu Y, Hu J, Li R, Li C, Liang B, Liu Y et al (2019) A prospective partial bio-based diamine-adenine-monomer platform for high performance polymer: a case study on phthalonitrile resin. Polym Degrad Stab 167:114–12310.1016/j.polymdegradstab.2019.06.023 ↗
45. Dong Y, Lam JW, Qin A, Li Z, Sun J, Sung HH et al (2007) Switching the light emission of (4-biphenylyl)phenyldibenzofulvene by morphological modulation: crystallization-induced emission enhancement. Chem Commun (Camb) 7:40–4210.1039/B613157C ↗
46. Du W, Lu J, Sun P, Zhu Y, Jiang X (2013) Organic salt-assisted liquid-phase exfoliation of graphite to produce high-quality graphene. Chem Phys Lett 568:198–20110.1016/j.cplett.2013.03.060 ↗
47. Carrasco PM, Montes S, García I, Borghei M, Jiang H, Odriozola I et al (2014) High-concentration aqueous dispersions of graphene produced by exfoliation of graphite using cellulose nanocrystals. Carbon 70:157–16310.1016/j.carbon.2013.12.086 ↗
48. Backes C, Paton KR, Hanlon D, Yuan S, Katsnelson MI, Houston J et al (2016) Spectroscopic metrics allow in situ measurement of mean size and thickness of liquid-exfoliated few-layer graphene nanosheets. Nanoscale 8:4311–432310.1039/C5NR08047A ↗
49. Narayan R, Lim J, Jeon T, Li DJ, Kim SO (2017) Perylene tetracarboxylate surfactant assisted liquid phase exfoliation of graphite into graphene nanosheets with facile re-dispersibility in aqueous/organic polar solvents. Carbon 119:555–56810.1016/j.carbon.2017.04.071 ↗
50. Sun Y, Chen L, Cui L, Zhang Y, Du X (2018) Molecular dynamics simulation of cross-linked epoxy resin and its interaction energy with graphene under two typical force fields. Comput Mater Sci 143:240–24710.1016/j.commatsci.2017.11.007 ↗
51. Caridad B, Paredes JI, Pérez Vidal O, Villar Rodil S, Pagán A, Cenis JL et al (2018) A biosupramolecular approach to graphene: complementary nucleotide-nucleobase combinations as enhanced stabilizers towards aqueous-phase exfoliation and functional graphene-nucleotide hydrogels. Carbon 129:321–33410.1016/j.carbon.2017.12.007 ↗
52. Ayán-Varela M, Paredes JI, Guardia L, Villar-Rodil S, Munuera JM, Díaz-González 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 7:10293–1030710.1021/acsami.5b00910 ↗
53. Sun J, Hu C, Liu Z, Liu H, Qu J (2019) Surface charge and hydrophilicity improvement of graphene membranes via modification of pore surface oxygen-containing groups to enhance permeability and selectivity. Carbon 145:140–14810.1016/j.carbon.2018.12.098 ↗